Journal of the American Chemical Society p. 525 - 528 (1982)
Update date:2022-08-16
Topics:
Midland, M. Mark
Zderic, Stephen A.
Second-order rate constants for the reaction of B-n-octyl-9-BBN with para-substituted benzaldehydes were obtained.Electron-withdrawing groups on the benzaldehyde increase the rate of reduction.The rate constants correlate with ?+ (ρ +1.03).Relative rates for reduction of para-substituted benzaldehydes with B-3-pinanyl-9-BBN gave a ρ of +0.49.The relative rates are consistent with a hydride addition to the carbonyl carbon in the rate-determining step.Activation parameters were obtained for the reaction of three benzaldehydes with B-n-octyl-9-BBN.The major barrier to the reaction is entropy.The large negative entropies of activation (-43 to -49 eu) indicate a highly ordered transition state.It is postulated that an organoborane-carbonyl oxygen complex is an intermediate in the reduction.
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