[C:1]1([Se]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].C1(S(Cl)=O)C=CC=CC=1.[OH:19][OH:20].C[CH2:22][O:23]CC>C(Cl)Cl>[C:22]([O:19][OH:20])(=[O:23])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
The diene (2) 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).
Wird geladen…
