G. Kramer, H. Brown
May 24, 1977
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Journal
Journal of Organometallic Chemistry
Abstract
Abstract Several B-allyl derivatives of 9-borabicyclo[3.3.1]nonane (9-BBN) were prepared either by the allylation of B-methoxy-9-BBN with allylic aluminum re-agents or by the monohydroboration of certain dienes and allenes with 9-BBN. The 1H NMR spectra of these derivatives were examined at various temperatures, revealing the presence of either permanent allylic rearrangements or cistrans isomerizations about the allylic double bond. The protonolyses of both B-allyl- and B-crotyl-9-BBN occur readily, giving propene in the former case and 1-butene in the latter, presumably via allylic rearrangement. Bromination of B-allyl-9-BBN leads to the formation of allyl bromide and B-bromo-9-BBN. Three mechanistic schemes are offered for this reaction. The hydroboration-oxidations of B-allyl- and B-crotyl-9-BBN were studied. The allyl derivative affords only 1,3-propanediol, while the crotyl isomer gives mostly 1,3-butanediol.