THE STEREOSELECTIVE ADDITION OF DIHALOCARBENES TO cistrans, trans-CYCLODODECA-1,5,9-TRIENE AND THE SYNTHESIS OF CYCLOTRIDECANONE

Author:

Nozaki H.,Katô S.,Noyori R.

Abstract

The addition reactions of dibromo- and dichloro-carbenes to cis,trans,trans-cyclododeca-1,5,9-triene (I) followed a stereoselective scheme analogous to that of other reagents forming a three-membered ring on addition to an olefinic bond. The carbenes attacked preferentially one of the trans double bonds of I and then added to the cis double bond of the resulting bicyclic cis,trans dienes. Skattebøl's ring cleavage of dihalocarbene adducts of cis-cyclo-dodecene as well as of the monoadducts of I, followed by several steps, gave cyclotridecanone in fairly good yields.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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