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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

Citation

Moorhoff, CM, Investigating the Mechanism of 1,3,5-Cycloheptatriene Formation: Condensation of 1-Methylethyl 3-Oxo-4-(triphenylarsoranylidene)butanoate with 7-Methoxy-3,7-dimethyloctanal, Heteroatom Chemistry, 9, (4) pp. 411-418. ISSN 1042-7163 (1998) [Refereed Article]

DOI: doi:10.1002/(SICI)1098-1071(1998)9:4<411::AID-HC9>3.0.CO;2-A

Abstract

Condensation of [3-(1-methylethoxy-carbonyl)-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 γ-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 γ-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. © 1998 John Wiley & Sons, Inc.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Moorhoff, CM (Dr Moorhoff)
ID Code:14137
Year Published:1998
Web of Science® Times Cited:1
Deposited By:Chemistry
Deposited On:1998-08-01
Last Modified:2011-08-09
Downloads:0

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