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The cycloaddition reaction of α-oxo sulfines and 2-trimethylsilyloxy-1,3-butadienes

✍ Scribed by J. B. M. Rewinkel; B. Zwanenburg

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
615 KB
Volume
109
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The cycloaddition reaction of α‐oxo sulfines with 2‐(trimethylsiloxy)‐1,3‐dienes, leading ultimately to thiacyclohexanone S‐oxides (alternatively named as thianone S‐oxides or perhydrothiapyranone S‐oxides) is described. 1‐Oxo‐2‐thioxo‐indane S‐oxide 2a, and several α‐oxo sulfines generated in situ have been studied. The cycloaddition reaction is regioselective, and thiacyclohexan–3‐one S‐oxides are the preponderant or the exclusive products. In the case of 1‐ethoxy‐3‐(tri‐methylsiloxy)‐1,3‐butadiene 3c the primary cycloadduct with sulfine 2a can either undergo mild hydrolysis to give a thiacyclohexan‐3‐one S‐oxide 6h or elimination to give thia‐4‐cyclohexen‐3‐one S‐oxide (2,6‐dihydrothiapyran‐3‐one S‐oxide) 6i. The regiochemistry of these cycloadditions is discussed in terms of HOMO/LUMO coefficients.

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