Muthiah, C. ; Praveen Kumar, K. ; Aruna Mani, C. ; Kumara Swamy, K. C. (2000) Chlorophosphonates: inexpensive precursors for stereodefined chloro-substituted olefins and unsymmetrical disubstituted acetylenes Journal of Organic Chemistry, 65 (12). pp. 3733-3737. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo991946y
Related URL: http://dx.doi.org/10.1021/jo991946y
Abstract
New chlorophosphonates bearing a 1,3,2-dioxaphosphorinane ring which are useful for the stereospecific synthesis of 5-chlorofurfuryl substituted olefins and chloro-substituted dienes have been obtained by an easy, inexpensive route. The utility of some of these in the synthesis of ferrocenyl- and anthracenyl-substituted unsymmetrical acetylenes has been explored. The structures of the phosphonates (OCH2CMe2CH2O)P(O)CH2(C4H2ClO) (4) and (OCH2CMe2CH2O)P(O)(CH=CHCH(Cl)Ph (7) have been determined; in addition, the stereochemistry of (5-chlorofurfuryl)CH=CH(4-ClC6H4) (13b) and 2,4-Cl2C6H3-CH=CH-CH=C(Ph)Cl (14a) is unambiguously proved by the X-ray structure determination.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 29597 |
| Deposited On: | 20 Dec 2010 07:59 |
| Last Modified: | 11 May 2012 10:26 |
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