56569-76-7Relevant articles and documents
Alkyl Migration in Competition with Phenylthio Migration in the Acid-catalysed Rearrangement of Alcohols
Hannaby, Malcolm,Warren, Stuart
, p. 3007 - 3014 (2007/10/02)
Sulfonate derivatives of conformationally rigid syn-2-phenylthiocyclohexanols, which are prevented from phenylthio migration by stereochemistry, rearrange slowly by alkyl migration or ring contraction.In contrast to other electronegative groups, phenylthio slows the reaction down but allows migration of other groups.
ALKYL MIGRATION INCLUDING RING CONTRACTION FROM A MIGRATION ORIGIN BEARING A PHENYLTHIO (PhS) GROUP
Hannaby, Malcolm,Warren, Stuart
, p. 1069 - 1072 (2007/10/02)
Alkyl shifts occur from tertary C atoms bearing a PhS group if PhS migration is prevented, but are retarded by the PhS group: the transition state has a cation-like migration terminus with little, if any, alkyl participation.
Fluoride-Mediated Reactions of Enol Silyl Ethers. Regiospecific Monoalkylation of Ketones
Kuwajima, Isao,Nakamura, Eiichi,Shimizu, Makoto
, p. 1025 - 1030 (2007/10/02)
Treatment of enol silyl ethers with alkyl halides in the presence of benzyltrimethylammonium fluoride and molecular sieves at room temperature gives the corresponding monoalkylated products with high regiospecificity.In most cases no polyalkylated products formed in the reaction.The alkylation reaction is highly chemospecific: esters, epoxides, and even ketones survive the reaction conditions.The reactions of various cyclohexanone derivatives proceed with the preferential axial attack of the electrophile.