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.

Citations

0

CrossRef
0

Web of Science
0

Scopus

Authors (2)

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

Cite as

Full text

full text is not available in portal

full content of the article see on external site open in new tab

Keywords

Details

Category:

Articles

Type:

artykuły w czasopismach

Published in:

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
ISSN: 1042-6507

Language:

English

Publication year:

2023

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 -, (2023),

DOI: