Addition reactions of conjugated double bonds. Part V. Stereochemistry of pyrazoline ring formation from αβ-unsaturated phenylhydrazones

Harry Ferres; Mohammad S. Hamdam; William R. Jackson

Addition reactions of conjugated double bonds. Part V. Stereochemistry of pyrazoline ring formation from αβ-unsaturated phenylhydrazones

Harry Ferres, Mohammad S. Hamdam, William R. Jackson

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

13 Citations (Scopus)

Abstract

The stereochemistry of cyclisation of the phenylhydrazones of some αβ-unsaturated ketones is discussed in terms of a stereoselective enamine-imine tautomerism step. Cyclisation of the phenylhydrazone of 1-acetyl-4-t-butyl-cyclohexene results in an initial axial attack of the nitrogen nucleophile on the six-membered ring.

Original language	English
Pages (from-to)	936-938
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	7
Publication status	Published - 1 Dec 1973

Cite this

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title = "Addition reactions of conjugated double bonds. Part V. Stereochemistry of pyrazoline ring formation from αβ-unsaturated phenylhydrazones",

abstract = "The stereochemistry of cyclisation of the phenylhydrazones of some αβ-unsaturated ketones is discussed in terms of a stereoselective enamine-imine tautomerism step. Cyclisation of the phenylhydrazone of 1-acetyl-4-t-butyl-cyclohexene results in an initial axial attack of the nitrogen nucleophile on the six-membered ring.",

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year = "1973",

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AU - Ferres, Harry

AU - Hamdam, Mohammad S.

AU - Jackson, William R.

PY - 1973/12/1

Y1 - 1973/12/1

N2 - The stereochemistry of cyclisation of the phenylhydrazones of some αβ-unsaturated ketones is discussed in terms of a stereoselective enamine-imine tautomerism step. Cyclisation of the phenylhydrazone of 1-acetyl-4-t-butyl-cyclohexene results in an initial axial attack of the nitrogen nucleophile on the six-membered ring.

AB - The stereochemistry of cyclisation of the phenylhydrazones of some αβ-unsaturated ketones is discussed in terms of a stereoselective enamine-imine tautomerism step. Cyclisation of the phenylhydrazone of 1-acetyl-4-t-butyl-cyclohexene results in an initial axial attack of the nitrogen nucleophile on the six-membered ring.

UR - http://www.scopus.com/inward/record.url?scp=37049127055&partnerID=8YFLogxK

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AN - SCOPUS:37049127055

SN - 1472-779X

SP - 936

EP - 938

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

IS - 7

ER -

Addition reactions of conjugated double bonds. Part V. Stereochemistry of pyrazoline ring formation from αβ-unsaturated phenylhydrazones

Abstract

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