A Novel [4+2] Cycloaddition Reaction Involving Lawesson’s Reagent. Structure and Specific Fragmentations of a New Cyclic 1,2-Thiaphosphinane-4-one

Witold Przychodzeń; Barbara Kusznierewicz

doi:10.1080/10426507.2023.2281477

A Novel [4+2] Cycloaddition Reaction Involving Lawesson’s Reagent. Structure and Specific Fragmentations of a New Cyclic 1,2-Thiaphosphinane-4-one

Abstract

A crude morpholine enamine of acetone treated with Lawesson’s reagent unexpectedly yielded a six-membered thiaphosphinane-4-one. This compound is the first example of a new class of heterocycles. It has been proven that it is formed from 4-methyl-2-morpholino-1,3-pentadiene which is usually present in crude morpholine enamine batches. A mechanism of this regioselective reaction was postulated and a characteristic chair-like conformation of the product was examined in detail. Additionally, some unusual primary fragmentations of the product with the loss of H2S and isobutylene were observed for positive and negative ESI ionization mode, respectively.

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Authors (2)

Witold Przychodzeń dr hab. inż.
Barbara Kusznierewicz dr hab. inż.

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Articles

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artykuły w czasopismach

Published in:

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS no. 199, pages 478 - 485,
ISSN: 1042-6507

Language:

English

Publication year:

2024

Bibliographic description:

Przychodzeń W., Kusznierewicz B.: A Novel [4+2] Cycloaddition Reaction Involving Lawesson’s Reagent. Structure and Specific Fragmentations of a New Cyclic 1,2-Thiaphosphinane-4-one// PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS -Vol. 199,iss. 6 (2024), s.478-485

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