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Investigating the mechanism of 1,3,5-cycloheptatriene formation: Condensation of 1-methylethyl 3-oxo-4-(triphenylarsoranylidene)butanoate with 7-methoxy-3,7-dimethyloctanal

✍ Scribed by Cornelius M. Moorhoff

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 244 KB
Volume: 9
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(1998)9:4<411::aid-hc9>3.0.co;2-a

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✦ Synopsis

-2-oxopropyl]triphenylarsonium bromide 8 with 7-methoxy-3,7-dimethyloctanal 10 in the presence of a base gave bis(1-methylethyl) 4,7-dihydroxy-2-(6-methoxy-2,6-dimethylheptyl)-3,5,7-cycloheptatriene-1,3-dicarboxylate 7b. The formation of 7b can be explained by a number of consecutive steps. The mechanism, strongly supported by liquid secondary ion mass spectrometry, suggests that an aldol condensation of the c-arsonium ylide 2b and the aldehyde 10 takes place as the initiating step and is followed by a Michael addition of the aldol product and the c-arsonium ylide 2b. Then an intramolecular nucleophilic substitution and elimination of triphenylarsine, followed by base-catalyzed elimination of a second molecule triphenylarsine takes place to produce 7b.

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