A Radical Cascade Cyclization To Prepare Dihydrothiophenes Induced by Thiyl Radicals as Sulfur Biradical Equivalents

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• 作者：Akio Kamimura ; Koichiro Miyazaki ; Yu Yamane ; Ryuichiro Yo ; Shingo Ishikawa ; Hidemitsu Uno ; Michinori Sumimoto
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：August 16, 2013
• 年：2013
• 卷：78
• 期：16
• 页码：7816-7822
• 全文大小：276K
• 年卷期：v.78,no.16(August 16, 2013)
• ISSN：1520-6904

文摘

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 S_Hi 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.