A novel [4+2] cycloaddition reaction involving Lawesson's reagent. Structure and specific fragmentations of a new cyclic 1,2-thiaphosphinane-4-one

被引：0

作者：

Przychodzen, Witold ^{[1
]}

Kusznierewicz, Barbara ^{[2
]}

机构：

[1] Gdansk Univ Technol, Fac Chem, Dept Organ Chem, 11-12 Narutowicza St, PL-80233 Gdansk, Poland

[2] Gdansk Univ Technol, Fac Chem, Dept Chem Technol & Biotechnol Food, Gdansk, Poland

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2024年 / 199卷 / 06期

关键词：

Lawesson's reagent; hetero Diels Alder reaction; 2-aminodienes; heterocycles; X-ray analysis; MS fragmentations; KETONES; DIENES; ROUTE;

D O I：

10.1080/10426507.2023.2281477

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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.

引用

页码：478 / 485

页数：8

共 34 条

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