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Reverse-Cope cyclisations of thiahydroxylamines derived from the addition of allylic thiols to nitrones: Syntheses of 1,3-thiazolidine-N-oxides and 1,5,2-oxathiazinanes

✍ Scribed by Michael P Coogan; Michael B Gravestock; David W Knight; Steven R Thornton

Book ID
104258300
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
238 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

AUylthiols 7 react as nucleophiles with nitrones 8 to give intermediate thiahydroxylamines which undergo reverse-Cope cyclisations to provide 1,3thiazolidine-N-oxides 9; in the case of derivatives of C-phenyl nitrone, thermolysis results in smooth Meisenheimer rearrangement leading to the 1,5,2-oxathiazinane 14.

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