Issue 122, 2015

In the searching for zwitterionic intermediates on reaction paths of [3 + 2] cycloaddition reactions between 2,2,4,4-tetramethyl-3-thiocyclobutanone S-methylide and polymerizable olefins

Abstract

DFT calculations show that – both in a weakly polar and in a strongly polar medium – the [3 + 2]-cycloaddition of 2,2,4,4-tetramethyl-3-thiocyclobutanone S-methylide with nitroethene takes place according to a polar, two-step mechanism with a zwitterionic intermediate. On the other hand, a similar reaction with less electrophilic t-butyl methacrylate is a single-step process. However, zwitterionic structures with “extended” conformation may be formed in both cases considered here, in a reaction path competitive to cycloaddition.

Graphical abstract: In the searching for zwitterionic intermediates on reaction paths of [3 + 2] cycloaddition reactions between 2,2,4,4-tetramethyl-3-thiocyclobutanone S-methylide and polymerizable olefins

Supplementary files

Article information

Article type
Communication
Submitted
07 okt 2015
Accepted
17 nov 2015
First published
18 nov 2015

RSC Adv., 2015,5, 101045-101048

In the searching for zwitterionic intermediates on reaction paths of [3 + 2] cycloaddition reactions between 2,2,4,4-tetramethyl-3-thiocyclobutanone S-methylide and polymerizable olefins

R. Jasiński, RSC Adv., 2015, 5, 101045 DOI: 10.1039/C5RA20747A

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