𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Base-Catalysed H-D Exchange in 1 -Methylthiolanium Iodide

✍ Scribed by G. Barbarella; A. Garbesi; A. Fava

Book ID
102252123
Publisher
John Wiley and Sons
Year
1971
Tongue
German
Weight
226 KB
Volume
54
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The kinetics of the base‐catalysed H/D exchange of the 1‐methylthiolanium cation in heavy water has been studied. Of the four α‐methylene protons, two exchange much faster than the other two, a result which requires that reprotonation of the carbanion intermediate occurs with retention of configuration. NMR. spectral analysis indicates that the protons undergoing faster exchange bear a trans relation to the lone‐pair on sulfur. This conclusion appears to conform to Wolfe's theory on the stability of carbanions [3].

πŸ“œ SIMILAR VOLUMES

Steric control in the base catalysed H-D
Steric control in the base catalysed H-D exchange of an Ξ±,Ξ²-unsaturated ketone
✍ Bruce A.W. Coller; W. Roy Jackson; Anna Stragalinou; JΕ±rgen U.G. Strauss πŸ“‚ Article πŸ“… 1979 πŸ› Elsevier Science 🌐 French βš– 128 KB

For the base catalysed H-D exchange of the equatorial hydrogen and the axial hydrogen in 4-t-butyl-1-acetylcyclohex-l-ene (1) in CH30D containing CH30Na, keq/kax is 3.8:1. This is clearly a result of steric rather than stereoelectronic factors.

Pt(II) - catalysed 1h-2h exchange in alk
Pt(II) - catalysed 1h-2h exchange in alkanes and cycloalkanes
✍ G.W. Littlecott; F.J. McQuillin πŸ“‚ Article πŸ“… 1973 πŸ› Elsevier Science 🌐 French βš– 191 KB

Gol\*dshleyerc !@abint Shilov and Steinman (1) preposed a reaoticol Soheme 1 for 'H -2H exchange of alkanas oatalysed by Pt(I1) chloride in AoOD and D20.