Thiocarbonyl Ylides VI. New Generation of Thiocarbonyl Ylides from Organosilicon Compounds Containing Sulfur and Their 1, 3-Cycloadditions

YOSHIYASU TERAO; MASAHIRO AONO; NOBUYUKI IMAI; KAZUO ACHIWA

doi:10.1248/cpb.35.1734

YOSHIYASU TERAO, MASAHIRO AONO, NOBUYUKI IMAI, KAZUO ACHIWA

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Keywords: thiocarbonyl ylide, 1, 3-cycloaddition, organosilicon compound, thermolysis, tetrahydrothiophene, regioselectivity

JOURNAL FREE ACCESS

1987 Volume 35 Issue 5 Pages 1734-1740

DOI https://doi.org/10.1248/cpb.35.1734

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Abstract

Thermolysis of bromo (trimethylsilyl) methyl trimethylsilylmethyl sulfide was found to give a thiocarbonyl ylide, the 1, 3-cycloaddition of which proved a new method for the synthesis of tetrahydrothiophenes. The effect of the silyl group of the ylide on the regio- and stereoselectivity in these 1, 3-dipolar cycloadditions is discussed.

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