Abstract
Adamantanethione S-methylide ( 5) is an easily accessible thiocarbonyl S-ylide. Generated by N 2 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 C-S hydrogenolyses. The CS group is an ambident electrophile; the ratios of regioisomeric adducts suggest that electronic effects favor the 4′,5′-substituted 1,3-dithiolanes, whereas steric effects support the 2′,4′-substituted systems. Electrophilic carbonyl compounds and 5 regiospecifically provide 2,4-disubstituted 1,3-oxathiolanes. Imines appear to be weak dipolarophiles vs. 5.
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