Dimethylsilanethione — Generation by retro-ene reaction and cycloaddition with ketene

Dimethylsilanethione was cleanly generated, under flash vacuum thermolysis conditions, by retro-ene cleavage of propargylthiodimethylsilane. The cothermolysis of this latter and ketene dimer led in 60 % yield to an only [2+2] cycloadduct, 2,2-dimethyl-4-methylene-2-sila-3-thiaoxetane, which in turn...

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Bibliographic Details
Published in:Tetrahedron letters 1996-09, Vol.37 (39), p.7017-7018
Main Authors: Lefèvre, Valérie, Dat, Yves, Ripoll, Jean-Louis
Format: Article
Language:English
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Summary:Dimethylsilanethione was cleanly generated, under flash vacuum thermolysis conditions, by retro-ene cleavage of propargylthiodimethylsilane. The cothermolysis of this latter and ketene dimer led in 60 % yield to an only [2+2] cycloadduct, 2,2-dimethyl-4-methylene-2-sila-3-thiaoxetane, which in turn can be cleaved at higher temperature to give hexamethylcyclotrisiloxane. Silane 4 gave silanethione 1 upon FVT. Cothermolysis of 4 and ketene dimer led to cycloadduct 5, which at higher temperature gave 6.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01532-8