Journal of the American Chemical Society p. 528 - 531 (1982)
Update date:2022-08-28
Topics:
Midland, M. Mark
Petre, Janet E.
Zderic, Stephen A.
Kazubski, Aleksander
B-Alkyl-9-BBN compounds undergo a slow olefin-alkyl group exchange when refluxed with an olefin in tetrahydrofuran.The half-life of the process for B-trans-2-methylcyclopentyl- and B-3-methyl-2-butyl-9-BBN is approximately 4 days.However, B-3-pinanyl-9-BBN undergoes an exceptionally rapid olefin-alkyl group exchange with a half-life of less than 10 h.Kinetic and competition experiments support a dehydroboration-hydroboration process.The isomerization of the B-3-pinanyl-9-BBN to B-myrtanyl-9-BBN, which one would expect to accompany such a facile dehydroboration, is not seen until 145 deg C.After 24 h at 165 deg C, the reaction reaches equilibrium with B-trans-myrtanyl-9-BBN as the major product.Treatment of this organoborane with benzaldehyde liberates the rare (+)-β-pinene.The facility with which B-3-pinanyl-9-BBN undergoes dehydroboration has important consequences for asymmetric reductions with this reagent.
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