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Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes

Kirkland, Thomas A. and Grubbs, Robert H. (1997) Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes. Journal of Organic Chemistry, 62 (21). pp. 7310-7318. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20180515-160418674

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Abstract

Ruthenium alkylidene 1 and molybdenum alkylidene 2 have been utilized in the ring-closing metathesis (RCM) of dienes containing gem-disubstituted olefins to yield tri- and tetrasubstituted cyclic olefins. Dienes with sterically demanding and/or electron-withdrawing substituents such as Ph, CO_2Me, and ^tBu were cyclized successfully with 2, but did not cyclize with 1. Tetrasubstituted cyclic olefins could be formed with 2, but not using alkylidene 1. Dienes with allylic functional groups yielded functionalized cyclic olefins when treated with 1.


Item Type:Article
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https://doi.org/10.1021/jo970877pDOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jo970877pPublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 1997 American Chemical Society. Received May 13, 1997. Publication Date (Web): October 17, 1997. The authors would like to thank Dr. Soong-Hoon Kim for providing a sample of 19b for comparison, Dr. Peter Schwab for providing alkylidene 1 and Dr. Osamu Fujimura and Mr. Delwin Elder for providing alkylidene 2. We wish to thank Dr. Nathan Dallesko and Dr. Peter Kondrat for providing mass spectral data. This work was supported by the NIH.
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Issue or Number:21
Record Number:CaltechAUTHORS:20180515-160418674
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180515-160418674
Official Citation:Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes. Thomas A. Kirkland and Robert H. Grubbs. The Journal of Organic Chemistry 1997 62 (21), 7310-7318 DOI: 10.1021/jo970877p
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86418
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:18 May 2018 17:51
Last Modified:03 Oct 2019 19:43

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