Letters in Organic Chemistry

Gwilherm Evano
Free University of Brussels
Brussels
Belgium

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Cyclodienyl 1,3-Dianionic Synthons: A Novel Synthesis of 5,5-Dimethyl- 1,3-Bis-(trimethylsilyl)cyclohexa-1,3-diene and its Diels-Alder [π4s+π2s] Cycloadditions with Six Dienophiles

Author(s): Venkatesh G. Bhoothappa, HariPrasad Suresh.

Abstract:

The synthesis of 5,5-dimethyl-1,3-bis(trimethylsilyl)cyclohexa-1,3-diene: a novel cyclic 1,3-dianionic synthon is reported by the Wurtz-Fittig coupling reaction of 1,3-dichloro-5,5-dimethylcyclohexa-1,3-diene with metallic sodium and chlorotrimethylsilane in anhydrous ether solvent. The compound on further Diels-Alder [π4s+π2s] cycloaddition with five N-substituted maleimides gave five novel cycloadducts: the N-substituted 11,11-dimethyl-1,8-bis(trimethylsilyl)-4- azatricyclo[5.2.2.02,6]undec-8-ene-3,5-diones; and reaction with maleic anhydride yielded the novel 11,11-dimethyl-1,8- bis(trimethylsilyl)-4-oxotricyclo[5.2.2.02,6]undec-8-ene-3,5-dione in 94-97% overall yields.

Keywords: 11, 11-dimethyl-1, 8-bis(trimethylsilyl)-4-aza-tricyclo[5.2.2.02, 6]undec-8-ene-3, 5-diones, 11, 11-dimethyl-1, 8- bis(trimethylsilyl)-4-oxo-tricyclo[5.2.2.02, 6]undec-8-ene-3, 5-diones, cyclic 1, 3-dianionic synthons, bis(trimethylsilyl)cyclohexadiene

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Article Details

VOLUME: 9
ISSUE: 10
Year: 2012
Page: [696 - 700]
Pages: 5
DOI: 10.2174/157017812803901872
Price: $58