title: A synthesis of (1E,3E)-TMS dienes from keto-xanthates via Chugaev-type elimination.
abstract: An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
authors.forename: Kelvin Kau Kiat
authors.initials: KK
authors.lastname: Goh
authors.forename: Sunggak
authors.initials: S
authors.lastname: Kim
authors.forename: Samir Z
authors.initials: SZ
authors.lastname: Zard