Reactions of some N-acyl-1-alkylamines with poly phosphoric ester PPE: nuclear magnetic resonance and stereochemistry of reaction products

Phenylindanes were obtained from the reaction of N-acyl-1-arylalkylamines with polyphosphoric ester (PPE). cis-1-Methyl-3-(3,4-dimethoxyphenyl)-5,6-dimethoxyindane was synthesized to determine which stereoisomer was produced by N-formyl and N-acetyl-1-(3,4-dimethoxyphenyl)ethylamine with PPE. Nuclea...

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Bibliographic Details
Published in:Canadian journal of chemistry 1987-11, Vol.65 (11), p.2568-2574
Main Authors: Alesso, Elba N, Tombari, Dora G, Iglesias, Graciela Y. Moltrasio, Aguirre, José M
Format: Article
Language:English
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Summary:Phenylindanes were obtained from the reaction of N-acyl-1-arylalkylamines with polyphosphoric ester (PPE). cis-1-Methyl-3-(3,4-dimethoxyphenyl)-5,6-dimethoxyindane was synthesized to determine which stereoisomer was produced by N-formyl and N-acetyl-1-(3,4-dimethoxyphenyl)ethylamine with PPE. Nuclear magnetic resonance specra ( 1 H and 13 C) of several mono-, 1,3-di-, and 1,2,3-tri-substituted indanes were fully analyzed to provide information on steric interactions and conformation of the cyclopentene ring. Possible cyclodimerization pathways are proposed.
ISSN:0008-4042
1480-3291
DOI:10.1139/v87-427