Perhydroazulenes. 6. 4-Keto Derivatives with Bridgehead Methyl Substituents1

Herbert O. House; Glenn S. Nomura; Don VanDerveer; Jane E. Wissinger

doi:10.1021/jo00363a002

Perhydroazulenes. 6. 4-Keto Derivatives with Bridgehead Methyl Substituents₁

Herbert O. House, Glenn S. Nomura, Don VanDerveer, Jane E. Wissinger

Chemistry (Twin Cities)

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Abstract

The two 9-methyl stereoisomers 3 and 4 and the two 10-methyl stereoisomers 8 and 9 of 4-ketoperhydroazulene have been prepared and fully characterized by means of spectra, analyses, and crystal structures. Several routes, including the selective methylation of the enone 2 to form the unsaturated ketone 12, were used (Schemes II and III) to form the 10-methyl compounds 8 and 9. Methylation of the lithium enolate (7) of 4-ketoperhydroazulene yielded a mixture of monoalkylated products containing 97% of the cis isomer 8 and 3% of the trans isomer 9. Probable conformations for the enolates and alkylated products obtained in this study are discussed.

Original language	English (US)
Pages (from-to)	2408-2416
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	51
Issue number	13
DOIs	https://doi.org/10.1021/jo00363a002
State	Published - Jan 1 1986

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abstract = "The two 9-methyl stereoisomers 3 and 4 and the two 10-methyl stereoisomers 8 and 9 of 4-ketoperhydroazulene have been prepared and fully characterized by means of spectra, analyses, and crystal structures. Several routes, including the selective methylation of the enone 2 to form the unsaturated ketone 12, were used (Schemes II and III) to form the 10-methyl compounds 8 and 9. Methylation of the lithium enolate (7) of 4-ketoperhydroazulene yielded a mixture of monoalkylated products containing 97% of the cis isomer 8 and 3% of the trans isomer 9. Probable conformations for the enolates and alkylated products obtained in this study are discussed.",

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T1 - Perhydroazulenes. 6. 4-Keto Derivatives with Bridgehead Methyl Substituents1

AU - House, Herbert O.

AU - Nomura, Glenn S.

AU - VanDerveer, Don

AU - Wissinger, Jane E.

PY - 1986/1/1

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N2 - The two 9-methyl stereoisomers 3 and 4 and the two 10-methyl stereoisomers 8 and 9 of 4-ketoperhydroazulene have been prepared and fully characterized by means of spectra, analyses, and crystal structures. Several routes, including the selective methylation of the enone 2 to form the unsaturated ketone 12, were used (Schemes II and III) to form the 10-methyl compounds 8 and 9. Methylation of the lithium enolate (7) of 4-ketoperhydroazulene yielded a mixture of monoalkylated products containing 97% of the cis isomer 8 and 3% of the trans isomer 9. Probable conformations for the enolates and alkylated products obtained in this study are discussed.

AB - The two 9-methyl stereoisomers 3 and 4 and the two 10-methyl stereoisomers 8 and 9 of 4-ketoperhydroazulene have been prepared and fully characterized by means of spectra, analyses, and crystal structures. Several routes, including the selective methylation of the enone 2 to form the unsaturated ketone 12, were used (Schemes II and III) to form the 10-methyl compounds 8 and 9. Methylation of the lithium enolate (7) of 4-ketoperhydroazulene yielded a mixture of monoalkylated products containing 97% of the cis isomer 8 and 3% of the trans isomer 9. Probable conformations for the enolates and alkylated products obtained in this study are discussed.

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Perhydroazulenes. 6. 4-Keto Derivatives with Bridgehead Methyl Substituents₁

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