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Reaction of 3-bromobenzyl and 3-bromoacetyl coumarin with phosphites. Synthesis of some new phosphonates and phosphates in the coumarin series

✍ Scribed by Rositca Nikolova; Anka Bojilova; Nestor A. Rodios


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
791 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis


The reaction of 3-(l-bromobenzyl)coumarin 3 with trialkyl phosphites afforded in good yields the corresponding dialkyl phosphonates 5, the Arbuzov reaction products. The interaction of trialkyl phosphites with 3-(co-bromoacetyl)coumarin 4 gave the corresponding dialkyl vinylphosphates 8 as the only isolated products, whereas dialkyl phosphites reacted with 4 under phase transfer catalysis and gave vinylphosphates 8 or dialkyl 1,2-epoxy-ethylphosphonates 9. The ~oxo-phosphonates 7 were obtained from the reaction of hydrazono-derivative 10 with trialkyl phosphitos and the subsequent hydrolysis of the dialkyl ]~-hydrazono-phosphonates 11 thus formed.


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