Affordable Access

Publisher Website

Organoboranes in organic synthesis:IX. Carbonylation products of organoboranes derived from myrcene

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
156
Issue
1
Identifiers
DOI: 10.1016/s0022-328x(00)84871-8

Abstract

Abstract Myrcene and thexylborane react in the ratio 2 3 to give a mixture of two boranes, only one of which is carbonylated with cyanide/trifluoroacetic anhydride, followed by oxidation, to give 3-hydroxymethyl-6-isopropyl-2-methylcyclohexanone (A). The positions of hydroboration are established by synthesis of the hydroboration/oxidation products. The cyanidation of the organoboranes derived from myrcene and diborane leads to a 2 3 mixture of A and 5-(2′-hydroxyethyl)-2-isopropylcyclohexanone, the structures of which are established by independent synthesis. The hydroboration of myrcene is shown to be relatively non-stereospecific.

There are no comments yet on this publication. Be the first to share your thoughts.