Conversion of cyclohexanone to spiro[3,4-cyclohexano-4-hydroxybicyclo[3.3.1]nonan-9-one-2,1′-cyclohexane]

George Pettit, Evan G. Thomas, Cherry L. Herald

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The course of cyclohexanone self-condensation, under a variety of reaction conditions, has been a classic problem for over 80 years. Self-condensation of cyclohexanone catalyzed by sodium methoxide-dimethylformamide has been shown to afford the title substance (10, mp 186.5-187°C) in 40% yield. Structural elucidation of ketol 10 was undertaken by degradative methods and provided the interesting series of products illustrated by structures 11-14, 16-21, and 23. Unequivocal confirmation for the skeletal arrangement of ketol 10 and the stereochemical assignments was obtained by solving the X-ray crystal structure.

Original languageEnglish (US)
Pages (from-to)4167-4171
Number of pages5
JournalJournal of Organic Chemistry
Volume46
Issue number21
StatePublished - 1981
Externally publishedYes

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Condensation
Dimethylformamide
Methanol
Crystal structure
X rays
Cyclohexane
cyclohexanone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Conversion of cyclohexanone to spiro[3,4-cyclohexano-4-hydroxybicyclo[3.3.1]nonan-9-one-2,1′-cyclohexane]. / Pettit, George; Thomas, Evan G.; Herald, Cherry L.

In: Journal of Organic Chemistry, Vol. 46, No. 21, 1981, p. 4167-4171.

Research output: Contribution to journalArticle

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abstract = "The course of cyclohexanone self-condensation, under a variety of reaction conditions, has been a classic problem for over 80 years. Self-condensation of cyclohexanone catalyzed by sodium methoxide-dimethylformamide has been shown to afford the title substance (10, mp 186.5-187°C) in 40{\%} yield. Structural elucidation of ketol 10 was undertaken by degradative methods and provided the interesting series of products illustrated by structures 11-14, 16-21, and 23. Unequivocal confirmation for the skeletal arrangement of ketol 10 and the stereochemical assignments was obtained by solving the X-ray crystal structure.",
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