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Thiofenchone s-methylide and its spiro-1,3,4-thiadiazoline precursor

✍ Scribed by Rolf Huisgen; Grzegorz Mloston; Albert Pröbstl

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
171 KB
Volume
12
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Spiro[fenchane‐2,2′‐(1,3,4)‐thiadiazoline] (6), prepared from thiofenchone and diazomethane, extrudes N~2~ (t~1/2~ 22 min, 46°C, toluene) and furnishes the S‐methylide 7 which, in turn, closes the thiirane ring or else is intercepted by 1,3‐cycloadditions to dipolarophiles (tetracyanoethylene, maleic anhydride, N‐methyl‐1,2,4‐triazoline‐3,5‐dione, aromatic thioketones). When thiocarbonyl S‐methylide 7 is set free in methanol, fenchone S,O‐dimethylacetal is formed as an HX adduct. Catalysis by acetic acid converts 7 to 1‐(methylthio)‐α‐fenchene (25) by way of a Wagner‐Meerwein rearrangement. The addition of diazomethane to thiocampher leads, via thiadiazoline 12, to thiocamphor S‐methylide; the latter undergoes a 1,4‐H shift, thus affording 2‐methylthio‐2‐bornene (11). © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:136–145, 2001

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