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The Acid-Catalyzed Cyclization of Acyclic Dienes

Ulery, H. E. and Richards, J. H. (1964) The Acid-Catalyzed Cyclization of Acyclic Dienes. Journal of the American Chemical Society, 86 (15). pp. 3113-3117. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20150430-135625008

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Abstract

The acid-catalyzed cyclizations of trans,trans- and cis,cis-2,6-octadiene have been investigated utilizing deuterated acid to initiate cyclization. The stereochemistry of the products shows that the cyclization process is concerted with proton attack and follows the stereoelectronic predictions made for terpene biosynthesis. A small percentage of the time the acquisition of the nucleophile is clearly concerted with the preceding steps and leads, likewise, to the theoretically expected product.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01069a028DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01069a028PublisherArticle
Additional Information:© 1964 American Chemical Society. Publication Date: August 1964. This work was supported in part by a grant from the Paint Research Institute and in part by Public Health Service Research Grant GM 10218-02.
Funders:
Funding AgencyGrant Number
Pain Research InstituteUNSPECIFIED
U. S. Public Health Service (USPHS)GM 10218-02
Issue or Number:15
Record Number:CaltechAUTHORS:20150430-135625008
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150430-135625008
Official Citation:The Acid-Catalyzed Cyclization of Acyclic Dienes H. E. Ulery and J. H. Richards Journal of the American Chemical Society 1964 86 (15), 3113-3117 DOI: 10.1021/ja01069a028
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57123
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:01 May 2015 02:36
Last Modified:03 Oct 2019 08:21

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