Tetrahedron

Cycloadditions of adamantanethione S-methylide to heteromultiple bonds

G Mloston, R Huisgen, K Polborn

Index: Mloston, Grzegorz; Huisgen, Rolf; Polborn, Kurt Tetrahedron, 1999 , vol. 55, # 38 p. 11475 - 11494

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Citation Number: 22

Abstract

Adamantanethione S-methylide (5) is an easily accessible thiocarbonyl S-ylide. Generated by N2 elimination from the cycloadduct of adamantanethione and diazomethane, the nucleophilic 1, 3-dipole 5 reacts in situ with thiocarbonyl compounds furnishing 1, 3- dithiolanes. 5 and carbon disulfide afford 1: 1 and 2: 1 cycloadducts. The structures are assessed by NMR spectra, a X-ray analysis, and CS hydrogenolyses. The C S group is ...

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