A synthesis of (±)-and (R)-muscone by radical ring expansion

Acta Chimica Sinica ›› 1995, Vol. 53 ›› Issue (9): 909-915. Previous Articles Next Articles

Original Articles

(±)-麝香酮和(R)-麝香酮的自由基扩环合成法

王大升;王道全;周长海

北京农业大学应用化学系

发布日期:1995-09-15

A synthesis of (±)-and (R)-muscone by radical ring expansion

WANG DASHENG;WANG DAOQUAN;ZHOU CHANGHAI

Published:1995-09-15

Abstract

In this paper, we report a new six-step synthesis of (±)-muscone (1) and nine-step synthesis of (R)-muscone (2) employing as their key step azobisisobutyronitrile and tri-n-butyltin hydride induced free radical ring expansion of α-ethoxycarbonyl-α -(2'-methyl-3'-phenylselenopropyl) cyclododecanone from the readily available cyclododecanone (3). The overall yields of 1 and 2 from 3 were 51% and 32% respectively.

Key words: INFRARED SPECTROPHOTOMETRY, PROTON MAGNETIC RESONANCE SPECTROMETRY, MUSCONE, FREE RADICALS

CLC Number:

O629

Cite this article

WANG DASHENG;WANG DAOQUAN;ZHOU CHANGHAI. A synthesis of (±)-and (R)-muscone by radical ring expansion[J]. Acta Chimica Sinica, 1995, 53(9): 909-915.

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(±)-麝香酮和(R)-麝香酮的自由基扩环合成法

A synthesis of (±)-and (R)-muscone by radical ring expansion

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