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Issue 122, 2015
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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

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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

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Publication details

The article was received on 07 Oct 2015, accepted on 17 Nov 2015 and first published on 18 Nov 2015


Article type: Communication
DOI: 10.1039/C5RA20747A
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Citation: RSC Adv., 2015,5, 101045-101048

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    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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