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The reaction of active and stabilized phosphonium ylides with α,β‐unsaturated carbonyl compounds [1]

The reaction of active and stabilized phosphonium ylides with α,β‐unsaturated carbonyl compounds [1] The active ketenylidene‐(2a) or thioketenylidenetriphenylphosphoranes (2b) react with 2‐benzylidene‐1,3‐indandione (1), 5‐benzylidenebarbituric acid (11), and 4‐benzylidene‐1,2‐diphenyl‐3,5‐pyrazolidinedione (16) to give the corresponding pyranones and thioxopyranones (3a,b, 12a,b) and (17a,b), respectively. On the other hand, compounds 1 and 11 can be converted by reaction with the stabilized alkylidenephosphoranes 4a–e into the phosphoranylidenes 6a–e and 13a–e. Moreover, the oxaphosphinins 8 or 14 and the oxazaphosphinins 10 or 15 were obtained when compounds 1 and 11 were allowed to react with the phosphorane 7 and the iminophosphorane 9, respectively. Some of these new organophosphorus compounds are found to have insecticidal and molluscicidal properties against cotton leafworm Spodoptera littoralis larvae and Biomphalaria alexandrina snails. © 1997 John Wiley, & Sons, Inc. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

The reaction of active and stabilized phosphonium ylides with α,β‐unsaturated carbonyl compounds [1]

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References (24)

Publisher
Wiley
Copyright
Copyright © 1997 Wiley Subscription Services
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/(SICI)1098-1071(1997)8:2<157::AID-HC8>3.0.CO;2-B
Publisher site
See Article on Publisher Site

Abstract

The active ketenylidene‐(2a) or thioketenylidenetriphenylphosphoranes (2b) react with 2‐benzylidene‐1,3‐indandione (1), 5‐benzylidenebarbituric acid (11), and 4‐benzylidene‐1,2‐diphenyl‐3,5‐pyrazolidinedione (16) to give the corresponding pyranones and thioxopyranones (3a,b, 12a,b) and (17a,b), respectively. On the other hand, compounds 1 and 11 can be converted by reaction with the stabilized alkylidenephosphoranes 4a–e into the phosphoranylidenes 6a–e and 13a–e. Moreover, the oxaphosphinins 8 or 14 and the oxazaphosphinins 10 or 15 were obtained when compounds 1 and 11 were allowed to react with the phosphorane 7 and the iminophosphorane 9, respectively. Some of these new organophosphorus compounds are found to have insecticidal and molluscicidal properties against cotton leafworm Spodoptera littoralis larvae and Biomphalaria alexandrina snails. © 1997 John Wiley, & Sons, Inc.

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 1997

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