Journal of Organic Chemistry p. 4468 - 4471 (1987)
Update date:2022-07-29
Topics:
Chou, Shang-Shing P.
Liou, Shyh-Yeon
Tsai, Chung-Ying
Wang, Ae-June
Sulfur-substituted 1,3-butadienes are useful reagents in organic synthesis.We now report two general methods for the regio- and stereoselective synthesis of substituted 2-(phenylthio)-1,3-butadienes 4 and 5. 3-(Phenythio)-3-sulfolenes 2 can be specifically alkylated at C5 under basic conditions.Extrusion of sulfur dioxide by lithium aluminum hydride then gives the dienes 4.On the other hand 2-substituted 3-sulfolenes 11 can be converted to the 3-phenylthio derivatives 9, which upon heating give the dienes 5.
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Doi:10.1021/ja01571a029
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