| 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. |
| Genre: | Article |
| ProdID: | 70006486 |
| Citation Author: | Abidi, S. L. |
| Citation Contributing Office: | Upper Midwest Environmental Sciences Center |
| Citation Datum: | |
| Citation Day: | 11 |
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| Citation End Page: | 2694 |
| Citation Issue: | 14 |
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| Citation Language: | English |
| Citation Larger Work Title: | Journal of Organic Chemistry |
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| Citation Month: | JUL |
| Citation No Pagination: | |
| Citation Number Of Pages: | 8 |
| Citation Online Only Flag: | |
| Citation Phsyical Description: | 8 p. |
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| Citation Public Comments: | None |
| Citation Publisher: | ACS Publications |
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| Citation Search Results Text: | Direct conversion of terpenylalkanolamines to ethylidyne N-nitroso compounds; 1986; Article; Journal; Journal of Organic Chemistry; Abidi, S. L. |
| Citation Start Page: | 2687 |
| Citation Volume: | 51 |
| Citation Year: | 1986 |
| Type: | citation/reference |
| Text: | Direct conversion of terpenylalkanolamines to ethylidyne N-nitroso compounds; 1986; Article; Journal; Journal of Organic Chemistry; Abidi, S. L. |
| URL (THUMBNAIL): | http://pubs.er.usgs.gov/thumbnails/outside_thumb.jpg |
| URL (DIGITAL OBJECT IDENTIFIER): | http://dx.doi.org/10.1021/jo00364a013 |
| Date Other: | Sun, 1 Jan 2012 11:01 -0600 |
| Publisher: | ACS Publications |
