Bromide ion → Perbenzoic acid

Participants

Reaction Conditions

Reaction Steps

The diene (2) of step (A) is treated with a halogenating agent such as phenylselenyl chloride or bromide or phenylsulfinyl chloride, preferably phenylselenyl chloride, in an approximately equimolar ratio in an inert solvent at about -80° C., for approximately 20 minutes; illustrative of such inert solvents are methylene chloride, ether and the like. After a standard workup the product residue is dissolved in an ethereal solvent, chilled to about 0° C. and oxidized with an agent such as 30% hydrogen peroxide or a peroxy acid such as peroxybenzoic acid to yield a halohydrin analog (3). Compound (3) is treated with nitrosyl chloride at a temperature between -10° and 10° C., preferably 0° C. for several minutes in a basic solvent until TLC analysis of an aliquot showed the reaction to be complete. Illustrative of such basic solvents are pyridine and quinoline and the like.

Provenance & Evidence