85894-92-4Relevant academic research and scientific papers
Improved and environmentally friendly large-scale preparation of cyclohexadienyl-, cycloheptadienyl sulfone and enantiopure epoxy cycloheptyl sulfones
Park, Taesik,Torres, Eduardo,Fuchs, Philip L.
, p. 1895 - 1900 (2007/10/03)
Kilogram-scale amounts of cycloheptadienyl phenylsulfone and cyclohexadienyl phenylsulfone were prepared by one operation in 5 stages with over 50% yield and requiring no purification. A practical and efficient method for the Jacobsen asymmetric epoxidati
Economical and environmentally friendly syntheses of 2-(phenylsulfonyl)-1,3-cyclohexadiene and 2-(phenylsulfonyl)-1,3-cycloheptadiene
Meyers, David J.,Fuchs, Philip L.
, p. 200 - 204 (2007/10/03)
A large-scale and inexpensive synthesis of dienes 1 and 2 has been developed via a four-step procedure starting with benzenethiol and the corresponding cyclic ketone. No chromatography is required.
ENOL THIOETHERS AS ENOL SUBSTITUTES. AN ALKYLATION SEQUENCE.
Trost,Lavoie
, p. 5075 - 5090 (2007/10/02)
Ionic bromination of enol phenyl thiolethers forms predominantly to exclusively 2-(phenylthio)-3-bromo-1-alkenes, an enolonium equivalent. The allylic bromide participates in displacements with stabilized and nonstabilized nucleophiles. The ability to hydrolyze the enol thioethers to their corresponding ketones equates this sequence to an equivalence of an enolonium ion. The versatility of the sulfur in selective introduction of allylic hydroxyl and amino groups as well as the ability to directly replace the sulfur substituent by hydrogen or alkyl imparts special significance to this approach. The sequence is highly regio-and chemoselective. Applications include the synthesis of lanceol and bisabolene and the introduction of steroid side chains.
