Bis(tert-butylsulfonyl)ethyne and 1-tert-butylsulfinyl-2-tert-butylsulfonylethyne

Abstract

The title compounds are electron-poor ethynes. The structure determination of bis(tert-butylsulfonyl)ethyne, C10H18O4S2, (I), is the first of a bis-sulfonyl-substituted ethyne. The molecule is situated on a crystallographic inversion centre. The S-Csp bond [1.737 (2) A] is the longest of this type reported to date. 1-tert-Butylsulfinyl-2-tert-butylsulfonylethyne, C10H18O3S2, (II), which is basically the same as (I) minus one O atom, crystallizes isomorphous with (I). This results in a nearly equal distribution of the three O atoms over the four possible positions.

Alkynes Between Main Group Elements: From Dumbbells via Rods to Squares and Tubes

“…Pericàs and co-workers found a procedure yielding quantitatively the desired product 382 by oxidizing bis( t -butylthio)acetylene ( 381 ) with m CPBA in chloroform (Scheme ) . Bis( t -butylsulfonyl)acetylene, the structural properties of which could even be elucidated by X-ray analysis, was widely used as a highly reactive dienophile in Diels−Alder reactions ,− and as alkyne component in highly electrophilic CpCo(monoalkyne) complexes. − Also bis(arylsulfonyl)acetylenes 385 and 386 were synthesized; however, a neutral oxidizing agent, such as dimethyldioxirane (DMDO), was necessary to achieve high yields (Scheme ); the corresponding products 385 and 386 could not be isolated without decomposition …”