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Long Range Splittings in the NMR Spectra of Isomeric 2-Bromo-2-butenes

Richards, John H. and Beach, William F. (1961) Long Range Splittings in the NMR Spectra of Isomeric 2-Bromo-2-butenes. Journal of Organic Chemistry, 26 (2). pp. 623-624. ISSN 0022-3263. doi:10.1021/jo01061a624. https://resolver.caltech.edu/CaltechAUTHORS:20150428-142630801

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Abstract

The recent publication of Fraser on long-range coupling between the protons in the methyl groups of tiglic and angelic acids and their methyl esters prompts us to report a similar observation in the NMR spectra of cis- and trans-2-bromo-2-butene. In this case, also, we observe coupling between the methyl group protons that are separated from one another by five bonds (four single bonds and one double bond). Furthermore, the magnitude of this coupling is larger when the two methyl groups are trans disposed about the olefinic linkage than when they are cis oriented. The possibilities of such splittings have been alluded to previously to account for the barely perceptible fine structure in one of the peaks in the NMR spectrum of methyl photosantonate. Such splittings across five bonds have also been observed in the NMR spectra of plumericin and in the spectra of other butene derivatives.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo01061a624DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo01061a624PublisherArticle
Additional Information:© 1961 American Chemical Society. Received June 9, 1960. Contribution No. 2584. Supported in part by a Public Health Service Grant E2775 from the National Institute of Allergy and Infectious Disease, U. S. Public Health Service. This investigation was carried out during the tenure of a Predoctoral Fellowship from the National Institute of Allergy and Infectious Diseases, U. S. Public Health Service.
Funders:
Funding AgencyGrant Number
National Institute of Allergy and Infectious DiseasesE-2775
NIH Predoctoral FellowshipUNSPECIFIED
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Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry2584
Issue or Number:2
DOI:10.1021/jo01061a624
Record Number:CaltechAUTHORS:20150428-142630801
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150428-142630801
Official Citation:Long Range Splittings in the NMR Spectra of Isomeric 2-Bromo-2-butenes John Richards and William Beach The Journal of Organic Chemistry 1961 26 (2), 623-624 DOI: 10.1021/jo01061a624
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57057
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:28 Apr 2015 21:39
Last Modified:10 Nov 2021 21:07

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