Hydroboration and Organic Synthesis: 9-Borabicyclo [3.3.1] by Ranjit S. Dhillon

By Ranjit S. Dhillon

This publication deals a scientific compilation of the big information on hand to man made chemists. It offers easy accessibility to the required info required for chemical transformations.

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Additional resources for Hydroboration and Organic Synthesis: 9-Borabicyclo [3.3.1] nonane (9-BBN)

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For example, B-cyclopentyl and B-trans2-methyl-cyclopentyl-9-BBN react very fast with benzaldehyde, whereas Bcyclohexyl and B-trans-2-methyl-cyclohexyl-9-BBN are usually slow reducing agents. 3) [12]. 3. Reaction of B-alkyl-9-BBN compounds with benzaldehyde to form olefin [5] (t1/2 is the time for 50% completion of reaction at reflux THF (65 °C)). The syn coplanar arrangement probably allows a maximum overlap of the developing π system of the displaced olefin. This need for coplanar B–C–C–H arrangement is also probably the cause for the large negative entropies.

03) [12]. 49. Electron-withdrawing groups increase the rate of reduction of substituted benzaldehydes. This effect is presumably also important for alkynyl ketones [7], where the small steric size of the acetylene and its negative inductive effect can combine to make the reduction possible. It is postulated that the reaction involves an organoborane–carbonyl oxygen complex as an intermediate in the reaction. The hydride transfer, k2, is presumably the rate-determining step (Eq. 21) [12]. 6 Kinetics of Complex Formation The complex formation of (9-BBN)2 with representative amines, which are more powerful nucleophiles than alcohols, are studied [1].

For example, B-cyclopentyl and B-trans2-methyl-cyclopentyl-9-BBN react very fast with benzaldehyde, whereas Bcyclohexyl and B-trans-2-methyl-cyclohexyl-9-BBN are usually slow reducing agents. 3) [12]. 3. Reaction of B-alkyl-9-BBN compounds with benzaldehyde to form olefin [5] (t1/2 is the time for 50% completion of reaction at reflux THF (65 °C)). The syn coplanar arrangement probably allows a maximum overlap of the developing π system of the displaced olefin. This need for coplanar B–C–C–H arrangement is also probably the cause for the large negative entropies.

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