A radical cascade cyclization to prepare dihydrothiophenes induced by thiyl radicals as sulfur biradical equivalents.

Abstract

Bicyclic dihydrothiophenes are readily prepared by a radical cascade cyclization reaction triggered by the addition of a thiyl radical under thermal or photoirradiation conditions. The translocated radical attacks the sulfur atom in the initial radical donor unit in an SHi manner. Sufficient stereoselectivity is achieved when a large excess of disulfide is used for the reaction under photoirradiation conditions. The reaction in the absence of solvents provides vinylsulfides instead of dihydrothiophenes. Thus, the sulfur atom in the thiyl radical serves as a sulfur biradical synthetic equivalent.

DOI: 10.1021/jo400975t

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Cite this paper

@article{Kamimura2013ARC, title={A radical cascade cyclization to prepare dihydrothiophenes induced by thiyl radicals as sulfur biradical equivalents.}, author={Akio Kamimura and Koichiro Miyazaki and Yu Yamane and Ryuichiro Yo and S. Ishikawa and Hidemitsu Uno and Michinori Sumimoto}, journal={The Journal of organic chemistry}, year={2013}, volume={78 16}, pages={7816-22} }