CaltechAUTHORS
  A Caltech Library Service

Synthesis of Substituted Bicyclo[2.2.2]octatrienes

Wagaman, Michael W. and Bellmann, Erika and Cucullu, Michèle and Grubbs, Robert H. (1997) Synthesis of Substituted Bicyclo[2.2.2]octatrienes. Journal of Organic Chemistry, 62 (26). pp. 9076-9082. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20180522-152355313

[img] PDF (^1H and ^(13)C NMR spectra for compounds 17a and 16b−19b (13 pages)) - Supplemental Material
See Usage Policy.

330Kb

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20180522-152355313

Abstract

An efficient route to bicyclo[2.2.2]octatriene, barrelene, and substituted versions of this molecule has been developed starting from the benzene equivalent cis-3,5-cyclohexadiene-1,2-diol. Following the Diels−Alder reaction of this molecule with an activated acetylene, conversion of the diol to the final olefin was accomplished through formation of a thiocarbonate intermediate and subsequent reaction with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine (DPD). The synthesis developed allows a variety of barrelenes to be prepared in as few as three steps from commercially available starting materials.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jo971039yDOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jo971039yPublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 1997 American Chemical Society. Received June 10, 1997. Publication Date (Web): December 26, 1997. Financial support for this research was provided by the Office of Naval Research, the U.S. Air Force, and the Ballistic Missiles Defense Organization through an AASERT grant. We also thank Dr. D. G. H. Ballard and ICI for their gift of cis-3,5-cyclohexadiene-1,2-diol.
Funders:
Funding AgencyGrant Number
Office of Naval Research (ONR)UNSPECIFIED
Air Force Office of Scientific Research (AFOSR)UNSPECIFIED
Ballistic Missiles Defense OrganizationUNSPECIFIED
Issue or Number:26
Record Number:CaltechAUTHORS:20180522-152355313
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180522-152355313
Official Citation:Synthesis of Substituted Bicyclo[2.2.2]octatrienes. Michael W. Wagaman, Erika Bellmann, Michèle Cucullu, and Robert H. Grubbs. The Journal of Organic Chemistry 1997 62 (26), 9076-9082 DOI: 10.1021/jo971039y
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86559
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:24 May 2018 16:39
Last Modified:03 Oct 2019 19:45

Repository Staff Only: item control page