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Synthesis of N ‐methyl‐3‐aza[10] paracyclophane: A rigid analog of phenethylamine
Author(s) -
Wu GengShuen,
Martinelli I. C.,
Btanton C. Dewitt,
Cox Richard H.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140103
Subject(s) - chemistry , ring (chemistry) , phenethylamine , dimethylaniline , stereochemistry , ethanol , ethylene , medicinal chemistry , organic chemistry , catalysis
The synthesis of N ‐methyl‐3‐aza[10]paracyclophane is reported which represents the first example of this ring system being formed via an acyloin reaction. This 3‐aza[10]paraeyclophane ring system behaves physiochemically inbetween the normal [9]‐ and [10]paracyclophane ring systems. Reductive desulfurization of N ‐methyl‐3‐aza[10]paracyclophane‐6‐ethylene thioketal in ethanol provides a small amount of the title compound and an unexpected, ring‐opened product, N ‐ethyl‐ N ‐methyl‐ p ‐heptylphenethylamine. A possible mechanism for the ring‐opening process is suggested.