3-Dimethylsulphonioindolide. An unusually basic crystalline sulphonium ylide

Abstract

3-Dimethylsulphonioindolide, an unusually THE stable, crystalline ylide (1) has been prepared and obbasic, crystalline ylide when dissolved in CDCI, or served t o possess unusual properties; in CDC1, or CD,OD CD,OD incorporates deuterium into the methyl groups. solutions a t or near room temperature i t incorporates

Indole 3-sulfonium ylides and related sulfonium salts. Carbon and hydrogen nuclear magnetic resonance study

“…Tables I and II contain the and 13C chemical shifts, respectively, for ylides (1), thioethers (2), and sulfonium salts (3). The methyl carbon shift in 2-methylindole (Table II) is sufficiently shielded to clearly separate 2-methyl and 5-methyl + Varian Associates.…”

“…The 5-methyl 13C resonances for thioethers 2a-c appear at higher field than the corresponding resonances for the ylides (la-c) in accord with the behavior of the respective hydrogen resonance shifts. However, although the differences are small (1-2 ppm), the 13C resonances of ylide (1) 5-methyls occur downfield of sulfonium salt (3) 5 Effects on C-2 and C-3 of Substitution at These Sites. It is well established that C-2 of iodole is relatively electron deficient whereas C-3 is the site of highest carbon electron density.…”

Direkter Ylidtransfer auf Carbonylverbindungen und Heteroarene

“…(2)]. [21] Der auffallend leichte Zugang zu 6 a ermutigte uns, auch zu 5 a verwandte Verbindungen auf ihre Eignung in der Ylidtransferreaktion zu untersuchen.…”