Stereochemistry of nitrogen heterocycles. 68. Stereochemistry of 2,5-dimethyl-4-piperidone, 2,5-dimethyl-4-piperidol, and their N-benzoyl derivatives

Litvinenko, G. S.; Voronenko, L. A.; Krasnomolova, L. P.

doi:10.1007/bf00472753

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“…The conformational studies of various 2,6-dimethyl, 2.6-diethyl and 2,6-diphenylpiperidone derivatives [1][2][3][4][5][6][7][8][9] exhibited normal chair conformation. The same type of compounds i.e., 3-isopropylpiperidin-4-one derivatives are prepared and also done conformational studies (Manimekali et al 10) .…”

Section: Introductionmentioning

confidence: 99%

Conformational Studies of Some N-Acyl-3- Ethylpiperidin-4-Ones

Selvaraju¹,

Manimekalai²

2018

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Section: Introductionmentioning

confidence: 99%

Conformational Studies of Some N-Acyl-3- Ethylpiperidin-4-Ones

Selvaraju¹,

Manimekalai²

2018

RJC

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Unusual Conformational Behavior of 3,7-Dihetera(N,N-;N,O-;N,S-) Bicyclo[3.3.1]Nonan-9-Ols Via Nmr Analysis

Yu¹,

Berlin

Iskakova³

et al. 2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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Based upon the analysis of 1 H NMR data, along with molecular modeling, it was shown that the reduction of 3,7-dihetera(N,N-; N,O-; N,S-)bicyclo[3.3.1]nonan-9-ones by LiAlH 4 led to a mixture of two stereoisomeric secondary alcohols with different orientations of the hydroxyl groups in one of the ring systems. Diaza derivatives in deuterochloroform exist in predominant chair-boat conformations. However, the replacement of nitrogen in one of the heterocycles by oxygen or sulfur led to stereoisomers one of which existed in chair-boat conformation and another in a chair-chair conformation. In all cases the boat conformation is stabilized by formation of an intramolecular hydrogen bond (IMHB) between a lone electron pair of the nitrogen atom and a proton on the pseudo axial hydroxyl group of the other ring.

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Stereochemistry of nitrogen heterocycles. 68. Stereochemistry of 2,5-dimethyl-4-piperidone, 2,5-dimethyl-4-piperidol, and their N-benzoyl derivatives

Cited by 2 publications

References 5 publications

Conformational Studies of Some N-Acyl-3- Ethylpiperidin-4-Ones

Conformational Studies of Some N-Acyl-3- Ethylpiperidin-4-Ones

Unusual Conformational Behavior of 3,7-Dihetera(N,N-;N,O-;N,S-) Bicyclo[3.3.1]Nonan-9-Ols Via Nmr Analysis

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