Te-1-Acylmethyl and Te-1-Iminoalkyl Telluroesters: Synthesis and Thermolysis Leading to 1,3-Diketones and O-Alkenyl and O-Imino Esters

Abstract

A series of Te-1-acylmethyl carbotelluroates was prepared in good isolated yields from the reaction of potassium carbotelluroates with α-haloketones in acetonitrile. Thermolysis of the telluroesters afforded vinyl esters in 20−50% yields, while treatment of the carbotellurorates with potassium t-butanolate led to 1,3-diketones in 30−75% yields with the liberation of black tellurium. The reaction of potassium carbotelluroates with α-haloaceto oximes gave O-acyl oximes in 50−70% yields via Te-1-iminomethylcarbotelluroates.

Keywords:

• 1,3-Diketones
• detelluration
• O-acyl iminoesters
• Te-1-acylmethyl carbotelluroates
• telluroesters
• thermolysis

Acknowledgments

Dedicated to Professor Naomichi Furukawa on the occasion of his 70th birthday.

This research was supported partially by a Grant-in-Aid for Scientific Research on Priority Areas from the Ministry of Education, Science, Sports and Culture of Japan. Nippon Soda Co., Ltd. kindly provided a sample of 3-chloro-2,6-dimethoxybenzoyl chloride.