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Muthiah C, Kumar KP, Mani CA, Kumara Swamy KC: Chlorophosphonates: inexpensive precursors for stereodefined chloro-substituted olefins and unsymmetrical disubstituted acetylenes. J Org Chem. 2000 Jun 16;65(12):3733-7. 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 (OCH (2) CMe (2) CH (2) O) P (O) CH (2)(C (4) H (2) ClO) (4) and (OCH (2) CMe (2) CH (2) O) P (O)(CH=CHCH (Cl) Ph (7) have been determined; in addition, the stereochemistry of (5-chlorofurfuryl) CH=CH (4-ClC (6) H (4)) (13b) and 2, 4-Cl (2) C (6) H (3)-CH=CH-CH=C (Ph) Cl (14a) is unambiguously proved by the X-ray structure determination. |
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