Volume 22, Issue 15
Preparative Organic Chemistry
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ChemInform Abstract: Reduction of Substituted Nitro Compounds with Tri-n-butyltin Hydride.

W. R. BOWMAN

W. R. BOWMAN

Dep. Chem., Loughborough Univ. Technol., Loughborough, Leics. LE11 3TU, UK

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D. CROSBY

D. CROSBY

Dep. Chem., Loughborough Univ. Technol., Loughborough, Leics. LE11 3TU, UK

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P. J. WESTLAKE

P. J. WESTLAKE

Dep. Chem., Loughborough Univ. Technol., Loughborough, Leics. LE11 3TU, UK

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First published: April 16, 1991

Abstract

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ChemInform Abstract

α-Substituted nitro compounds such as (I), (III), and (VI) are reduced by the title hydride to give the corresponding nitroalkanes. Applying low tributyltin hydride concentration the nitroalkane (VIIb) is accompanied by (VIII), a product of cyclization. No cyclic products are observed in the reduction of (IX), indicating that the bimolecular reduction of the intermediate α-nitroalkyl by Bu3SnH is faster than cyclization.

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