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Direct conversion of terpenylalkanolamines to ethylidyne N-nitroso compounds

Journal of Organic Chemistry

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DOI: 10.1021/jo00364a013

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Abstract

A series of mono- and diterpenylalkanolamines bearing isopropylidene functionality on the terpene group was reacted with sodium nitrite in aqueous acetic acid to yield ethylidyne N-nitroso analogues. The key feature of this direct conversion involved initial N-nitrosation followed by apparent elimination of a "CH4" unit (not necessarily methane) from the isopropylidene double bond. The product distribution data for ethylidyne nitrosamines derived from tertiary terpenyl alkanolamines reflect the conformational outcome of the nitrosative dealkylation process. For β,γ-unsaturated allylic diterpenylethanolamines, electronic effects appeared to be important for controlling the product distribution of ethylidyne nitrosamines in light of the highly selective α-cleavage observed in the nitrosation reactions.

Additional Publication Details

Publication type:
Article
Publication Subtype:
Journal Article
Title:
Direct conversion of terpenylalkanolamines to ethylidyne N-nitroso compounds
Series title:
Journal of Organic Chemistry
DOI:
10.1021/jo00364a013
Volume
51
Issue:
14
Year Published:
1986
Language:
English
Publisher:
ACS Publications
Publisher location:
Washington, D.C.
Contributing office(s):
Upper Midwest Environmental Sciences Center
Description:
8 p.
Larger Work Type:
Article
Larger Work Subtype:
Journal Article
Larger Work Title:
Journal of Organic Chemistry
First page:
2687
Last page:
2694
Number of Pages:
8