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Addition of hydrogen cyanide to 9-methyl- Δ4-octalone-3 and 9β-methyl-8β-hydroxy- Δ4-octalone-3

Banerjee, DK and Angadi, VB (1965) Addition of hydrogen cyanide to 9-methyl- Δ4-octalone-3 and 9β-methyl-8β-hydroxy- Δ4-octalone-3. In: Tetrahedron, 21 (3). pp. 281-289.

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Official URL: http://dx.doi.org/10.1016/S0040-4020(01)98269-9

Abstract

Addition of hydrogen cyanide to 9-methyl-Δ4-octalone-3 (IIb), as a model, yielded both cis- and trans-ketonitriles the configurations of which are assigned on the basis of IR spectra of the hydrolysed products. Similar addition of hydrogen cyanide to 9β-methyl-8β-hydroxy-Δ4-octalone-3 (IIc) gave the corresponding cis- and trans-hydroxy-keto-nitriles, configurations of which were proved by their conversion into cis- and trans-keto-nitriles obtained in the model study. In contrast to the model experiment where the trans-product predominated, the cis-isomer was the major product of addition to IIc.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 19 May 2010 06:18
Last Modified: 19 Sep 2010 06:06
URI: http://eprints.iisc.ernet.in/id/eprint/27912

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