Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter June 2, 2014

Zum Cycloreversionsmechanismus von 3.3-Bis(trifluormethyl)-2.2-dihydro-1.4.2-oxazaphosphol-4-enen [1] / Cycloreversion Mechanism of 3,3-Bis(trifluoromethyl)-2,2-dihydro-l,4,2- oxazaphosphol-4-enes [1]

  • Klaus Burger , Stephan Tremmel , Gabriele Trost , Reinhold Simmerl and Dieter Hübl

Abstract

2,2,2-Trimethoxy-3,3-bis(trifluoromethyl)-2,2-dihydro-1,4,2-oxazaphosphol-4-enes on thermolysis undergo a 1,3-dipolar cycloreversion reaction with formation of bis(trifluoro-methyl) substituted nitrile ylides. Trapping reactions of the 1,3-dipolar species with α,β-unsaturated carboxylic acid esters and nitriles are described. 2-Aryl-3-carbethoxy-5,5-bis(trifluoromethyl)-1-pyrrolines obtained undergo an uncatalyzed autoxidation pro-cess to give 2-aryl-3-carbethoxy-3-hydroxy-5,5-bis(trifluoromethyl)-1-pyrrolines. 5,5-Di-fluoro-4-trifluoromethyl-2-oxazolines and 5-fluoro-4-trifluoromethyl-oxazoles formed as by-products indicate that the thermal induced [3+2]-cycloreversion reaction of 2,2,2-tri-methoxy-3,3-bis(trifluoromethyl)-2,2-dihydro-1,4,2-oxazaphosphol-4-enes is most likely a stepwise process.

Received: 1983-1-24
Published Online: 2014-6-2
Published in Print: 1983-6-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Downloaded on 19.3.2024 from https://www.degruyter.com/document/doi/10.1515/znb-1983-0620/html
Scroll to top button