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Does the dieckmann condensation occur in the gas phase?

✍ Scribed by Mark J. Raftery; John H. Bowie

Publisher: John Wiley and Sons
Year: 1988
Tongue: English
Weight: 287 KB
Volume: 23
Category: Article
ISSN: 1076-5174
DOI: 10.1002/oms.1210231008

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✦ Synopsis

Burinsky and Cooks' have reported that deprotonated dimethyl adipate eliminates methanol via a gas-phase Dieckmann condensation. This is in contrast to the behaviour of simple methyl ester enolates which lose MeOH by a different mechanism, e.g. MeOCOCHCH,R + [M&(OCCHCH,R)] + O-C-CHCHR + MeOH. Evidence is presented which supports the Dieckmann mechanism for adipates. For example, MeOCOC(Me)CH,CH,CD(Me)COzMe should eliminate MeOD in a Dieckmann condensation, but MeOH by the alternative mechanism outlined above. Experimentally, MeOD is lost exclusively. Similarly, MeOCO~CH,CH,C(Me),CO,Me also loses MeOD, consistent with a Dieckmann process

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