Altering the Stereochemistry of Allylation Reactions of Cyclic α-Sulfinyl Radicals with Diarylureas

Article abstract of DOI:10.1021/jo00091a007

Radical allylations of 2-(phenylseleno)tetrahydrothiophene oxide and 2-benzyl-5-(phenylseleno)-3-isothiazolidone 1-oxide with allyltributylstannane in the presence of N,N-bis<3-(trifluoromethyl)-5-(carbooctyloxy)phenyl> urea have been investigated.This urea was shown to be about as selective as promoting formation of trans-2-allyltetrahydrothiophene oxide and trans-5-allyl-2-benzyl-3-isothiazolidone 1-oxide as hydrogen bonding solvents and Lewis acids.