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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^†

Corresponding Author

Cornelius M. Moorhoff

Department of Chemistry, University of Tasmania, GPO Box 252-75 Hobart, Tasmania, Australia 7001

Division of Molecular Science, CSIRO, Private Bag 10, Clayton South MDC, Victoria 3169, AustraliaSearch for more papers by this author

Cornelius M. Moorhoff,

Corresponding Author

Cornelius M. Moorhoff

Department of Chemistry, University of Tasmania, GPO Box 252-75 Hobart, Tasmania, Australia 7001

Division of Molecular Science, CSIRO, Private Bag 10, Clayton South MDC, Victoria 3169, AustraliaSearch for more papers by this author

First published: 07 December 1998

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

Citations: 1

^†

Dedicated to Prof. Heinrich Nöth on the occasion of his seventieth birthday.

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Abstract

Condensation of [3-(1-methylethoxycarbonyl)-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. Heteroatom Chem 9:411–418, 1998

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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^†

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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†

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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^†