Direct conversion of terpenylalkanolamines to ethylidyne N-nitroso compounds
Journal of Organic Chemistry
None
By: S. L. Abidi
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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.
| 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 |
| Google Analytic Metrics | Metrics page |