Substitution régiosélective d'arènesulfonylhydrazones α,β-insaturées via la réaction de Shapiro

Caille, Jean Claude; Farnier, Michel; Guilard, Roger

doi:10.1139/v86-135

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~Tablissement Des Structures1

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1986

2010

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Cited by 12 publications

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“…Enfin, la configuration des hydrazones 5 et 6 est diffkrente : en effet, de f a~o n classique (2b), l'hydrazone 5 est Z, alors que nous avons montrC dans l'article prCcCdent (1) que la configuration E de l'hydrazone 4 est conservCe lors de sa transformation en 6. Conclusion L'application de la rCaction de Shapiro des hydrazones de cyclopentanones constitue une voie d'accks aisCe ?…”

Section: ~Tablissement Des Structuresunclassified

Sur une nouvelle méthode de synthèse de δ-lactones cyclopenténiques

Caille¹,

Farnier²,

Guilard³

et al. 1986

Can. J. Chem.

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Synthesis of two cyclopentenic 6-lactones, 1,3,4,4a,5,6-hexahydrocyclopenta[c]pyran-1-one and its analogue possessing a cyclopentenyl group bonded to the carbon atom 4a is described, starting from the cyclopentanone or cyclopentylidene cyclopentanone. The remarkable reactivity of the tosylhydrazones allows transformation of these compounds into substituted cyclopentenes, which lead to 6-lactones by cyclization. The conditions of cyclization depend on the nature of the cyclopentanone. The structure of the two 6-lactones is established by 'H and I3C nIIx data, mass spectrometry, and, in one case, by X-ray analysis.

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Section: ~Tablissement Des Structuresunclassified