Triphenylphosphine Dibromide (PPh₃Br₂) Is More Than Just a Brominating Reagent: Experimental Selection Logic from Alcohol-to-Alkyl Bromide Conversion to Carboxylic Acid Activation and One-Pot Esterification, Vinyl Bromide Formation, and Nitrile Constructi

Introduction

Triphenylphosphine dibromide (triphenylphosphine dibromide, PPh₃Br₂) is often classified as a brominating reagent, but its representative value in organic synthesis lies in more than simply “providing a bromine source.” Existing reagent overviews and methodological studies show that PPh₃Br₂ can be used not only for converting alcohols into alkyl bromides, but also for carboxylic acid activation and one-pot esterification, for the construction of vinyl bromides via vinyl phosphate intermediates, and for promoting the dehydration of aromatic or heteroaromatic aldoximes to nitriles. Taken together, these results show that PPh₃Br₂ is a task-oriented reagent that combines phosphonium-type activation features with bromide-transfer capability: its real significance often lies in directing oxygen-containing substrates into reaction nodes better suited for the next operation, rather than merely accomplishing a superficial “bromination.”

From a mechanistic standpoint, PPh₃Br₂ can serve in dichloromethane as a source of the phosphonium-type activating species [Ph₃PBr]⁺Br⁻, which helps explain why in many reactions it tends to display a “pre-activation followed by transformation” profile rather than behavior dominated simply by free bromine. This article focuses on four experimentally relevant task types: alcohol-to-alkyl bromide conversion, carboxylic acid activation and one-pot esterification, conversion of ketones to vinyl bromides via vinyl phosphate intermediates, and dehydration of aldoximes to nitriles.

1. Four Experimental Tasks for Which PPh₃Br₂ Deserves Priority Consideration

Core Task	Main Transformation	Key Value	Situations in Which It Merits Priority Consideration
Alcohol-to-alkyl bromide conversion	ROH → RBr	Achieves transformation through activation-based substitution, especially suitable for substrates that require both functional-group compatibility and retention of stereochemical information	When the substrate is sensitive to elimination, rearrangement, or stereochemical outcome, and a more predictable substitution pathway is desired for bromination
Carboxylic acid activation and one-pot esterification	RCO₂H → acyl-activated species / ester	Carries the carboxylic acid directly into the subsequent bond-forming step, without separately isolating a highly reactive acyl halide	When carboxylic acid activation and subsequent esterification are to be integrated into a single system, minimizing the separate preparation and handling of highly reactive intermediates
Conversion of ketones to vinyl bromides via vinyl phosphate intermediates	ketone → vinyl phosphate → vinyl bromide	Converts carbonyl substrates into halogenated precursors better suited for subsequent coupling or further functionalization	When the target product itself is a vinyl bromide, and a two-step design involving initial construction of a phosphorus-containing leaving-group intermediate followed by bromination is acceptable
Dehydration of aldoximes to nitriles	aldoxime → nitrile	Demonstrates that its role has expanded into dehydration-based construction	When the substrate is an aromatic or heteroaromatic aldoxime and dehydration under relatively mild conditions is desired to directly access the nitrile product

2. Decision Logic for the Four Core Experimental Tasks

2.1 Alcohol-to-Alkyl Bromide Conversion: Activation-Based Substitution and Suitability for Sensitive Substrates

One of the most classical and best-supported uses of PPh₃Br₂ is the conversion of alcohols into the corresponding alkyl bromides. Relevant reagent reviews indicate that it can be used to convert both alcohols and phenols into bromides, although the main representative applications still center on alcohol substrates, especially alcohols bearing sensitive functional groups. Such reactions generally proceed through phosphonium activation followed by bromide substitution; in many systems this reduces elimination and molecular rearrangement, and for alcohol substrates amenable to SN2-type substitution, inversion of configuration is commonly observed. It is therefore particularly suitable for substrates where alkene compatibility, functional-group tolerance, or stereochemical outcome must be taken into account. Phenol conversion may be retained as an extended application, but the representative evidence currently remains centered primarily on alcohol substrates.

2.2 Carboxylic Acid Activation and One-Pot Esterification: Direct Entry from Carboxylic Acids into Subsequent Bond Formation

The representative value of PPh₃Br₂ in carboxylic acid transformations lies mainly in its ability to integrate carboxylic acid activation and subsequent esterification into a single system. Salomé and Kohn reported that carboxylic acids can be converted directly into esters in the presence of excess PPh₃Br₂, base, and alcohol, in yields of 30–95%; low racemization can be achieved with chiral acids, while the configuration at the alcohol terminus can be retained when chiral alcohols are used. The study further proposed that this pathway may be associated with an acyloxyalkoxyphosphorane-type intermediate formed during the reaction.

The practical significance of this route is that it allows the carboxylic acid to enter directly into the subsequent bond-forming process, reducing the need for separate preparation, isolation, and handling of highly reactive acyl halides. Aliphatic and aromatic acids do not behave identically in this route, and conditions usually need to be adjusted according to substrate type; accordingly, it should not be understood as a universal method equally applicable to all carboxylic acids.

2.3 Conversion of Ketones to Vinyl Bromides via Vinyl Phosphate Intermediates: Entering Vinyl Halide Precursors from Carbonyl Substrates

This route does not involve direct one-step conversion of a ketone to a vinyl bromide by PPh₃Br₂. Rather, the ketone first forms the corresponding vinyl phosphate intermediate, which is then converted into a vinyl halide by a triphenylphosphine dihalide reagent. In this transformation, PPh₃Br₂ serves as the halogenating reagent in the downstream stage. Its value lies in enabling common carbonyl substrates to be directed into vinyl halide precursors, thereby facilitating subsequent coupling or further functionalization. This route is distinct from α-bromination of carbonyl compounds: the former is a stepwise “ketone → vinyl phosphate → vinyl halide” sequence, whereas the latter is direct halogenation at the carbonyl α-position.

2.4 Dehydration of Aldoximes to Nitriles: Direct Entry from Aldoximes into Nitrile Construction

PPh₃Br₂ can also be used for the dehydration of aldoximes to nitriles. Representative studies have shown that aromatic and heteroaromatic aldoximes can be converted into the corresponding nitriles in acetonitrile at room temperature, with good results. This application indicates that the scope of PPh₃Br₂ has expanded from substitution and carboxylic acid activation into dehydration-based construction. The scope established in the literature so far is mainly limited to aromatic and heteroaromatic aldoximes; it should not be directly extrapolated to aliphatic or more complex oxime substrates without first checking for relevant precedent.

3. PPh₃Br₂ Occupies Different Reaction Levels in These Four Tasks

Experimental Task	Where PPh₃Br₂ Enters the Process	Characteristic Route Level	Implications for Experimental Design
Alcohol-to-alkyl bromide conversion	Acts directly on the starting substrate	A direct activation–substitution-type transformation	Focus on substrate compatibility, control of elimination/rearrangement, and stereochemical outcome
Carboxylic acid activation and one-pot esterification	First activates the carboxylic acid, then connects to the subsequent bond-forming step	A one-pot transformation that concatenates activation and bond formation	Focus on the type of carboxylic acid, matching between alcohol and base, and whether a one-pot workflow is appropriate
Conversion of ketones to vinyl bromides via vinyl phosphate intermediates	Enters at the downstream stage after formation of the intermediate	A downstream halogenation step within a stepwise route	Focus on whether the intermediate can be formed appropriately and whether the downstream halogenation can proceed smoothly
Dehydration of aldoximes to nitriles	Acts directly on the preformed oxime substrate	A functional-group dehydration-based construction	Focus on whether the substrate falls within the established scope and whether the dehydration proceeds cleanly

4. Three Misjudgments That Should Be Eliminated Before Experimental Selection

1. For routine, simple alcohol bromination, PPh₃Br₂ need not be assumed to be the default first choice.

The main advantages of PPh₃Br₂ lie in its relatively well-defined activation–substitution pathway and in its control over elimination, rearrangement, and compatibility with sensitive functional groups. If the substrate itself is not sensitive, these advantages may not be fully manifested.

2. α-Bromocarbonyl compounds and vinyl bromide precursors correspond to different transformation goals.

α-Bromocarbonyl compounds arise from direct halogenation at the carbonyl α-position, whereas conversion of ketones to vinyl bromides via vinyl phosphate intermediates is a stepwise transformation organized through an intermediate. The target products and experimental designs are therefore not the same.

3. The representative evidence for aldoxime dehydration to nitriles is concentrated mainly on aromatic and heteroaromatic substrates.

The currently clearer results are established mainly on aromatic and heteroaromatic aldoximes. For a broader substrate scope, the applicability of the method should be evaluated first before deciding whether to adopt this route.

5. Product Navigation Table for Experimental Selection Around Triphenylphosphine Dibromide (Choose Table 1–Table 4 According to Research or Experimental Objective)

Research or Experimental Objective	Which Table to Consult First	Why This Table Should Be Prioritized	Which Table to Read in Parallel	Navigation Notes
To first build an overall understanding of the PPh₃Br₂ reaction system and distinguish the core reagent, comparison brominating reagents, phosphorus-containing activating components, and typical byproducts	Table 1	Table 1 brings together the core framework components of the system, including triphenylphosphine dibromide, triphenylphosphine, phosphorus tribromide, phosphorus pentabromide, NBS, carbon tetrabromide, phosphorus-containing activating components, and triphenylphosphine oxide; it is the best starting point for clarifying which chemicals truly participate in activation and comparative evaluation	Then Table 2	First sort out the activation system, comparison systems, and byproduct-identification components; then move on to solvents, bases, and specific substrates for clearer downstream decision-making
To compare the differing reaction roles of triphenylphosphine dibromide versus phosphorus tribromide, NBS, and Appel-type phosphine/halogen systems, and determine which bromination pathway should be chosen	Table 1	Table 1 lists the core phosphine–bromine systems and classical comparison reagents, making it most suitable for horizontal comparison of reaction strength, activation mode, side reactions, and workup characteristics	Then Tables 2 and 3	First use Table 1 to determine which bromination/activation logic is involved; then consult Tables 2 and 3 for actual applicability under different conditions and with different substrates
To carry out experiments converting alcohol substrates to bromides, especially comparing how primary alcohols, secondary alcohols, allylic alcohols, and related substrates behave under phosphine–bromine conditions	Table 3	Table 3 centers on benzyl alcohol, cyclohexanol, cinnamyl alcohol, and their representative brominated products, making it suitable for direct evaluation based on substrate type and transformation outcome	Then Tables 1 and 2	First confirm the substrate and target product in Table 3, then return to Table 1 for the reagent system and Table 2 for solvents and bases to complete the experimental route
To study carboxylic acid activation and one-pot esterification, comparing the selection of different carboxylic acid frameworks, alcohol nucleophiles, and base systems	Table 3	Table 3 includes key substrates and representative products such as glacial acetic acid, benzoic acid, phenylacetic acid, (R)-mandelic acid, acetyl bromide, and methyl benzoate, making it suitable for first determining how the carboxylic acid component should be selected	Then Tables 2 and 1	Carboxylic acid activation routes require simultaneous consideration of the acid, alcohol, and base; first use Table 3 to define substrates and targets, then Table 2 to supplement methanol, ethanol, isopropanol, n-octanol, and acid-scavenging bases, and finally return to Table 1 for activating reagents and comparison systems
To focus on stereochemical retention, racemization control, and condition sensitivity in activation–esterification processes involving chiral carboxylic acids or chiral alcohols	Table 3	Table 3 contains representative substrates such as (R)-mandelic acid and (-)-menthol, which more clearly reflect stereochemical information and are suitable for screening centered on stereochemical retention and the relevant condition range	Then Table 2	In such studies, Table 3 provides the key chiral substrates, while Table 2 is better suited to supplement the influence of solvents and bases on stereochemical outcome
To start from ketones and construct vinyl bromide precursors, and to judge whether aliphatic ketones, aromatic ketones, and cyclic ketones are suitable for this route	Table 4	Table 4 focuses on chemicals related to methyl ethyl ketone, acetophenone, cyclohexanone, and the oxime/nitrile route, making it suitable for first assessing from the perspective of carbonyl substrate types and target products which transformations are accessible	Then Tables 1 and 2	First confirm substrate scope in Table 4; if strict correspondence to the literature route “ketone → vinyl phosphate → vinyl bromide” is required, the exact type of phosphorus-containing activating component must be checked further; Table 1 is more suitable for understanding the overall logic of such phosphorus-based leaving-group routes
To construct nitriles from aldoxime dehydration, or to plan the entire upstream-to-downstream route from “aldehyde/ketone → oxime → nitrile”	Table 4	Table 4 places hydroxylamine hydrochloride, α-benzaldoxime, and benzonitrile in the same table, making it suitable for selection in the order of “upstream oxime formation → downstream dehydration to nitrile”	Then Tables 1 and 2	First use Table 4 to sort out the substrate chain, then return to Table 1 for the core phosphine–bromine reagent and to Table 2 for common condition components such as acetonitrile, pyridine, and triethylamine
To begin from workup, system identification, and result confirmation, and determine which chemicals are more suitable for byproduct identification, product reference, and condition screening	Tables 1 and 3	Table 1 contains a typical byproduct reference such as triphenylphosphine oxide, while Table 3 contains representative products such as benzyl bromide, bromocyclohexane, acetyl bromide, and methyl benzoate, making them suitable for analytical selection and result confirmation	Then Tables 2 and 4	This type of task is not simply about finding a substrate; byproducts, target products, and conditions all need to be considered together. Therefore, Tables 1 and 3 should be read together first, and then Table 2 or Table 4 can be added back according to the specific task

Table 1 | Core Phosphine–Bromine Activation System, Comparative Brominating Reagents, and Byproduct Identification Components

Category	CAS No.	Aladdin Cat. No.	Name	Grade or Purity	Product Features and Applications
Core phosphine–bromine activating reagent	1034-39-5	T302116	Triphenylphosphine dibromide	≥95%	Combines phosphonium-type activation characteristics with bromide-transfer capability, and can be used in transformations such as alcohol-to-alkyl bromide conversion, carboxylic acid activation and one-pot esterification, and dehydration of aldoximes to nitriles.
Upstream phosphine source for PPh₃Br₂	603-35-0	T104475	Triphenylphosphine	≥99% (GC)	An important phosphine source for PPh₃Br₂ and Appel-type halogenation systems; used to construct phosphorus-containing activation systems and also serves as a precursor reference for the formation of triphenylphosphine oxide.
Classical phosphorus-based brominating reagent for comparison	7789-60-8	P108401	Phosphorus tribromide	PrimorTrace™, ≥99.99% metals basis	A classical reagent for converting alcohols to alkyl bromides; suitable for comparison with PPh₃Br₂ in terms of reaction strength, functional-group compatibility, and side-reaction control.
Strong phosphorus-based brominating reagent for comparison	7789-69-7	P109536	Phosphorus pentabromide	≥95%	More reactive and suitable for acyl or hydroxyl bromination under stronger conditions; appropriate as a comparison to the milder PPh₃Br₂ route.
Appel-type bromination comparison component	558-13-4	T106847	Carbon tetrabromide	≥99%	Commonly used together with triphenylphosphine in classical Appel-type bromination; suitable for comparing the operational differences between preformed PPh₃Br₂ and in situ phosphine/halogen systems.
Selective bromination reagent for comparison	128-08-5	B105057	N-Bromosuccinimide (NBS)	AR, ≥99%	Commonly used for allylic, benzylic, or radical bromination; suitable for distinguishing these pathways from the activation–substitution bromination mode of PPh₃Br₂.
Phosphorus-containing activator / phosphoryl chloride comparison component	2524-64-3	D109475	Diphenyl phosphoryl chloride	≥97%	Can be used as a comparison reference for phosphorus-containing activation components, helping to understand the route in which a ketone first forms a phosphorus-containing leaving-group intermediate and then enters the vinyl halide pathway; if strict correspondence to the representative ketone → vinyl phosphate → vinyl bromide conditions is required, the exact phosphoryl chloride used should be further verified.
Phosphorus-containing byproduct / workup reference compound	791-28-6	T106098	Triphenylphosphine oxide	≥98%	A typical phosphorus-containing byproduct formed after reactions of PPh₃Br₂ and related phosphine reagents; commonly used as a reference in workup, purification, and mechanistic analysis.

Table 2 | Reaction Media, Bases, and Common Alcohol Components Used in Esterification

Category	CAS No.	Aladdin Cat. No.	Name	Grade or Purity	Product Features and Applications
Aprotic reaction solvent	75-09-2	D433565	Dichloromethane	Anhydrous, ≥99.8%, containing 40–150 ppm amylene as stabilizer	Suitable for water-free operations such as phosphine–bromine activation and alcohol-to-alkyl bromide conversion; helps maintain an aprotic environment and control side reactions.
Polar aprotic solvent / dehydration reaction medium	75-05-8	A119012	Anhydrous acetonitrile (ACN)	Anhydrous, ≥99.8%, H₂O ≤ 0.003%	A representative medium for dehydration of aldoximes to nitriles under PPh₃Br₂ conditions; also commonly used in one-pot esterification and some phosphorus-mediated activation–transformation processes.
Acid-binding base / basic additive	110-86-1	P111513	Pyridine	Anhydrous, ≥99.8%	Commonly used to scavenge HBr, promote substrate activation, and stabilize the course of the reaction; a typical basic medium in phosphorus/halogen systems.
Acid-binding base / non-nucleophilic base	121-44-8	T140677	Triethylamine	Anhydrous, ≥99.5%, water ≤ 50 ppm	Commonly used in carboxylic acid activation and one-pot esterification to help neutralize acid and drive esterification or substitution forward.
Common alcohol nucleophile for esterification	67-56-1	M140298	Methanol	Anhydrous, ≥99.8%, H₂O ≤ 100 ppm	Commonly used as a small-molecule alcohol nucleophile in one-pot esterification of carboxylic acids; suitable for rapidly establishing esterification conditions and obtaining representative methyl ester products.
Common alcohol nucleophile for esterification	64-17-5	E111989	Ethanol	Guaranteed reagent, water ≤ 0.3%	Commonly used for constructing ethyl esters after carboxylic acid activation; also suitable as a common alcohol nucleophile for comparing the compatibility of different alcohols in activation–bond-forming processes.
Common alcohol nucleophile for esterification	67-63-0	I119459	Isopropyl alcohol (IPA)	Anhydrous, ≥99.5%	Can be used to construct slightly more hindered isopropyl esters; suitable for comparing the reactivity of different alcohol nucleophiles in one-pot esterification.
Long-chain alcohol nucleophile / substrate for hydrophobic ester construction	111-87-5	O119679	n-Octanol	Moligand™, anhydrous, ≥99%	Suitable for evaluating the bond-forming performance of long-chain alcohols in carboxylic acid activation–esterification systems; can also be used to prepare more hydrophobic ester products.

Table 3 | Substrates and Representative Products Related to Alcohol-to-Alkyl Bromide Conversion and Carboxylic Acid Activation Pathways

Category	CAS No.	Aladdin Cat. No.	Name	Grade or Purity	Product Features and Applications
Aliphatic carboxylic acid activation substrate	64-19-7	A116166	Acetic acid	Guaranteed reagent, ≥99.5%	Can be used to examine the basic reactivity of a carboxylic acid entering a highly reactive acyl activation pathway under PPh₃Br₂ conditions and then proceeding further into one-pot esterification.
Aromatic carboxylic acid activation substrate	65-85-0	B433247	Benzoic acid	Sublimed grade, ≥99%	A representative substrate for aromatic carboxylic acid activation and esterification; suitable for comparison with aliphatic carboxylic acids in terms of reaction reactivity and condition requirements.
Benzylic carboxylic acid activation substrate	103-82-2	P1506271	Phenylacetic acid	AR, ≥99.0%	Combines an aromatic ring with a benzylic methylene feature; suitable for examining differences among carboxylic acid skeletons in activation and esterification.
Chiral carboxylic acid activation substrate	611-71-2	M107076	(R)-(-)-Mandelic acid	≥99%	Commonly used to investigate stereochemical retention and racemization control during carboxylic acid activation–esterification processes.
Representative substrate for benzylic alcohol bromination	100-51-6	B163018	Benzyl alcohol	Pharmaceutical grade, PharmPure™	A representative substrate for evaluating conversion of a primary alcohol into benzyl bromide through phosphine–bromine activation; useful for observing substitution efficiency and workup performance.
Representative substrate for secondary alcohol bromination	108-93-0	C110399	Cyclohexanol	Standard for GC, ≥99% (GC)	Suitable for comparing the reaction activity, selectivity, and elimination tendency of secondary versus primary alcohols in PPh₃Br₂ bromination.
Allylic alcohol / sensitive functional-group substrate	104-54-1	C110605	Cinnamyl alcohol	≥98%	Suitable for examining bromination compatibility of alkene-containing alcohol substrates under phosphine–bromine conditions, as well as control over addition, rearrangement, or elimination side reactions.
Phenol activation / transformation comparison substrate	108-95-2	P128316	Phenol	≥99%	Can be used as a phenolic hydroxyl substrate to observe its activation and transformation behavior in the PPh₃Br₂ system and compare its reactivity with that of benzyl alcohol, aliphatic alcohols, and related substrates; also suitable for distinguishing the applicable scope of phenolic versus alcoholic substrates in this system.
Chiral alcohol / configuration-retention evaluation substrate	2216-51-5	M107058	(1R,2S,5R)-(-)-Menthol	Standard for GC, ≥99.5% (GC)	Suitable for investigating stereochemical retention when a chiral alcohol participates in carboxylic acid activation–esterification.
Representative product of benzylic alcohol bromination	100-39-0	B108549	Benzyl bromide	Moligand™, ≥98% (GC), stabilized with propylene oxide	A typical primary alkyl bromide obtained from benzyl alcohol after phosphine–bromine activation; can be used as a reference for bromination efficiency and purification results.
Representative product of secondary alcohol bromination	108-85-0	B109675	Bromocyclohexane	≥98%	A representative product of cyclohexanol bromination; useful for comparing the success, failure, and side reactions of bromination across different alcohol substrates.
Reference compound for highly reactive acyl halides	506-96-7	A109619	Acetyl bromide	≥97%	Can be used as a reference compound for highly reactive acyl-transfer species of the acyl halide class, helping to understand the reaction level that may be entered after carboxylic acid activation.
Representative product of aromatic carboxylic acid esterification	93-58-3	M108588	Methyl benzoate	Standard for GC, ≥99.5% (GC)	A representative ester product formed from benzoic acid and methanol after activation; suitable for confirming esterification results and screening conditions.

Table 4 | Substrates, Key Upstream Reagents, and Products Related to the Ketone → Vinyl Halide Precursor Route and the Aldoxime → Nitrile Route

Category	CAS No.	Aladdin Cat. No.	Name	Grade or Purity	Product Features and Applications
Aliphatic ketone substrate	78-93-3	B1506360	2-Butanone	Spectroscopic grade, ≥99%	Can be used to evaluate the suitability of aliphatic ketones for entering the vinyl halide precursor route after passing through a phosphorus-containing leaving-group intermediate.
Aromatic ketone substrate	98-86-2	A103666	Acetophenone	Standard for GC, ≥99.5% (GC)	Suitable for examining the performance of aromatic ketones in constructing vinyl halide precursors after activation, and for comparison with aliphatic ketones and cyclic ketones.
Cyclic ketone substrate	108-94-1	C116454	Cyclohexanone	Standard for GC	A representative substrate for entering the vinyl halide precursor route from cyclic ketones; useful for evaluating the suitability of cyclic substrates.
Upstream reagent for oxime preparation	5470-11-1	H112477	Hydroxylammonium chloride	PrimorTrace™, ≥99.99% metals basis	Commonly used to prepare the corresponding oximes from aldehydes/ketones; a key upstream component linking carbonyl substrates to the PPh₃Br₂-mediated dehydration-to-nitrile route.
Aldoxime substrate for dehydration	622-31-1	T135657	α-Benzaldoxime	≥90% (GC)	A direct representative substrate for nitrile formation by dehydration with PPh₃Br₂; used to evaluate the conversion efficiency from aldoxime to aromatic nitrile.
Representative product of nitrile construction	100-47-0	B119686	Benzonitrile	Anhydrous, ≥99%	A typical product obtained after dehydration of benzaldoxime; can be used as a reference and analytical standard for the nitrile-construction route.

Note: The above are representative Aladdin products. For more product specifications, please refer to the product list at the end of the article or search the Aladdin website using the “product name/CAS/catalog number.”

References

[1] Garima. Triphenylphosphine Dibromide. Synlett. 2010;(9):1426-1427. doi:10.1055/s-0029-1219908.

[2] Salomé C, Kohn H. Triphenylphosphine Dibromide: A Simple One-pot Esterification Reagent. Tetrahedron. 2009;65(2):456-460. doi:10.1016/j.tet.2008.10.062.

[3] Kamei K, Maeda N, Tatsuoka T. A Practical Synthetic Method for Vinyl Chlorides and Vinyl Bromides from Ketones via the Corresponding Vinyl Phosphate Intermediates. Tetrahedron Letters. 2005;46(2):229-232. doi:10.1016/j.tetlet.2004.11.075.

[4] Darvish F, Movassagh B, Erfani M. Triphenylphosphine Dibromide: A Useful Reagent for Conversion of Aldoximes into Nitriles. Arabian Journal of Chemistry. 2015;8(6):865-867. doi:10.1016/j.arabjc.2012.09.008.

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