Dienol rearrangements catalyzed by nickel chloride

KS Kyler, A Bashir-Hashemi…

Index: Kyler, Keith S.; Bashir-Hashemi, A.; Watt, David S. Journal of Organic Chemistry, 1984 , vol. 49, # 6 p. 1084 - 1090

Full Text: HTML

Citation Number: 16

Abstract

The rearrangement of dienols R. & (OH) CH= CHC (X)= CR, which possess a nonterminal, aryltliio or alkylthio substituent was effected by using nickel chloride in aqueous tert-butyl alcohol at 60" C to furnish the vicinally substituted dienol R, C== CHCH= C (X) CR,(OH). Application of this rearrangement to 24-(methy1thio) cholesta-5, 22, 24-trien-20-01 provided 24-(methylthio) cholesta-5, 20 (22), 23-trien-25-01 and formed the basis for a new, five- ...