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Ring Inversion in Cycloheptane and in Cycloheptene Derivatives

Knorr, R. and Ganter, C. and Roberts, J. D. (1967) Ring Inversion in Cycloheptane and in Cycloheptene Derivatives. Angewandte Chemie International Edition in English, 6 (6). pp. 556-557. ISSN 0570-0833. http://resolver.caltech.edu/CaltechAUTHORS:20151026-114005304

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Abstract

Rapid pseudorotation [I] causes interconversion of substituent groups between "above" and "below" positions in cycloheptanes even at -150º[2] unless restrictions are imposed by bulky groups ^(12b.31). An especially interesting example of cycloheptane conformational preferences and rates of cycloheptane-ring inversion is provided by 4,5-transdibromo-1,1-difluorocycloheptane (m.p. = 52-54 ºC). This substance was prepared from 4-cycloheptenone via several steps.


Item Type:Article
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http://dx.doi.org/10.1002/anie.196705562DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.196705562/abstractPublisherArticle
Additional Information:© 1967 Verlag Chemie. Received: April 10th, 1967. German version: Angew. Chem. 79, 577 1967. Dedicated to Professor G. Wittig on the occasion of his 70th birthday.
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Caltech Gates and Crellin Laboratories of Chemistry3511
Record Number:CaltechAUTHORS:20151026-114005304
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151026-114005304
Official Citation:Knorr, R., Ganter, C. and Roberts, J. D. (1967), Ring Inversion in Cycloheptane and in Cycloheptene Derivatives. Angew. Chem. Int. Ed. Engl., 6: 556–557. doi: 10.1002/anie.196705562
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ID Code:61521
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:04
Last Modified:26 Oct 2015 21:04

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