Preparation of trans,trans,trans- and cis,cis,trans-perhydrophenalen-9-ols by application of the three-migration cyanoborate process to isomeric perhydro-9b-boraphenalenes: differences between the cyanoborate and carbonylation reactions

Abstract

Application of the three-migration cyanoborate process to cis,cis-perhydro-9b-boraphenalene gives trans,trans,trans-perhydrophenalen-9-ol, in contrast to carbonylation which gives the cis,cis,cis-isomer; cis-trans-perhydro-9b-boraphenalene gives cis,cis,trans-perhydro-phenalen-9-ol by either process.