Proximity Effects in Fused Cyclobutanones. Facile Formation of Cage Systems

A. Hassner; Simba Naidorf-Meir; H. E. Gottlieb; I. Goldberg

doi:10.1021/jo00034a045

Proximity Effects in Fused Cyclobutanones. Facile Formation of Cage Systems

A. Hassner^*, Simba Naidorf-Meir, H. E. Gottlieb, I. Goldberg

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Chlorobicyclooctanone 3 on reaction with H₂O‒Et₃N in acetonitrile at 20 °C produced in high yield four complex dimeric compounds 4‒7. The novel structures produced by C‒C bond formation between tertiary centers were revealed by NMR and X-ray diffraction. Pathways leading from 4 or its diastereomer 14 to cage compounds 5‒7 indicate the importance of proximity effects in these transformations.

Original language	English
Pages (from-to)	2442-2445
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	57
Issue number	8
DOIs	https://doi.org/10.1021/jo00034a045
State	Published - 1 Apr 1992

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abstract = "Chlorobicyclooctanone 3 on reaction with H2O‒Et3N in acetonitrile at 20 °C produced in high yield four complex dimeric compounds 4‒7. The novel structures produced by C‒C bond formation between tertiary centers were revealed by NMR and X-ray diffraction. Pathways leading from 4 or its diastereomer 14 to cage compounds 5‒7 indicate the importance of proximity effects in these transformations.",

author = "A. Hassner and Simba Naidorf-Meir and Gottlieb, {H. E.} and I. Goldberg",

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AU - Goldberg, I.

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N2 - Chlorobicyclooctanone 3 on reaction with H2O‒Et3N in acetonitrile at 20 °C produced in high yield four complex dimeric compounds 4‒7. The novel structures produced by C‒C bond formation between tertiary centers were revealed by NMR and X-ray diffraction. Pathways leading from 4 or its diastereomer 14 to cage compounds 5‒7 indicate the importance of proximity effects in these transformations.

AB - Chlorobicyclooctanone 3 on reaction with H2O‒Et3N in acetonitrile at 20 °C produced in high yield four complex dimeric compounds 4‒7. The novel structures produced by C‒C bond formation between tertiary centers were revealed by NMR and X-ray diffraction. Pathways leading from 4 or its diastereomer 14 to cage compounds 5‒7 indicate the importance of proximity effects in these transformations.

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Proximity Effects in Fused Cyclobutanones. Facile Formation of Cage Systems

Abstract

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