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Further Information

Related Reactions
Mitsunobu Reaction5US WHT 8 LE Saucony SIL SIZE PROGRID 2 ECHELON wcSwqBHZ8
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Synthesis of alkyl bromides
Synthesis of alkyl chlorides

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The reaction of triphenylphosphine and tetrahalomethanes (CCl4, CBr4) with alcohols is a ready method to convert an alcohol to the corresponding alkyl halide under mild conditions. The yields are normally high.

This reaction is somewhat similar to the Mitsunobu Reaction, where the combination of a phosphine, a diazo compound as a coupling reagent, and a nucleophile are used to invert the stereochemistry of an alcohol or displace it.

Mechanism of the Appel Reaction

The reaction proceeds by activation of the triphenylphosphine by reaction with the tetrahalomethane, followed by attack of the alcohol oxygen at phosphorus to generate an oxyphosphonium intermediate. The oxygen is then transformed into a leaving group, and an SSpring Black UK3 US5 For Studded CN34 Stiletto Shoes Fall Basic Knee High Heel Pointed Boots Pu EU35 Women'S Casual Pump Red Toe Beige RTRY Boots Stiletto Pu Boots EU35 US5 Knee Black Women'S Boots Toe Basic Fall Casual Heel Shoes RTRY UK3 Spring Pump Studded High Red CN34 Beige For Pointed N2 displacement by halide takes place, proceeding with inversion of configuration if the carbon is asymmetric.

Recent Literature

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ROMPgel-Supported Triphenylphosphine with Potential Application in Parallel Synthesis
E. Arstad, A. G. M. Barrett, B. T. Hopkins, J. Koebberling, Org. Lett., 2002, 1975-1977.

Conversion of alcohols to bromides using a fluorous phosphine
L. Desmaris, N. Percina, L. Cottier, D. Sinou, Tetrahedron Lett.adidas Lux Women’s Alphabounce W Black Trainers RRPwTa7xq, 2003, High Stiletto For Casual Boots Spring Basic Heel Boots EU35 Fall Knee Studded US5 CN34 Beige Pu RTRY Toe UK3 Pump Women'S Black Red Pointed Shoes 44, 7589-7591.

Stoichiometric bromotrichloromethane in acetonitrile can replace solvent quantities of carbon tetrachloride in the synthesis of gem-dichloroalkenes from aldehydes in the presence of triphenylphosphine. Similarly, bromotrichloromethane in dichloromethane can be used for the Appel reaction of benzyl alcohols to form benzyl chlorides at r.t., which is commonly carried out in refluxing carbon tetrachloride.
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The facile preparation of alkenyl metathesis synthons
T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron, 2004, 60, 10943-10948.

Catalysis of Phosphorus(V)-Mediated Transformations: Dichlorination Reactions of Epoxides Under Appel Conditions
R. M. Denton, X. Tang, A. Przeslak, Org. Lett., 2010, 12, 4678-4681.

Chemoselective Isomerization of Secondary-Type Propargylic Alcohols to Propargylic/Allenic Bromides, and Brominated Dienes with Appel-Type Reaction Conditions
N. Sakai, T. Maruyama, T. Konakahara, Synlett, 2009, 2105-2106.

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