CaltechAUTHORS
  A Caltech Library Service

Small-Ring Compounds. XXVI. Nucleophilic Displacement Reactions of Some Halogen-substituted Phenylcyclobutenones

Caserio, Marjorie C. and Simmons, Howard E., Jr. and Johnson, A. Earl and Roberts, John D. (1960) Small-Ring Compounds. XXVI. Nucleophilic Displacement Reactions of Some Halogen-substituted Phenylcyclobutenones. Journal of the American Chemical Society, 82 (12). pp. 3102-3106. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151020-105600096

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: http://resolver.caltech.edu/CaltechAUTHORS:20151020-105600096

Abstract

Displacement reactions between alkali hxlides and several cyclic allylic-type halides, namely, 2,2-dihalo-3-phenylcyclo,-butenones, have been found to proceed with rearrangement to give 2,4-dihalo-3-phenylcyclobutenones. The 2,2-dihalocompounds also were found to rearrange to the corresponding allylic isomers on heating with triethylamine. The allylic iodides, 2-fluoro-4-iodo- and 2-chloro-4-iodo-3-plienyl-2-cyclobutenones,rearranged in reactions with halogens to form 2,2-dihalo-3-phenylcyclobutenones. Evidence is presented for the stereospecific nature of these reactions.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01497a030DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01497a030PublisherArticle
Additional Information:© 1960 American Chemical Society. Received November 6, 1959. Supported in part by the National Science Foundation.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry2446
Record Number:CaltechAUTHORS:20151020-105600096
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151020-105600096
Official Citation:Small-Ring Compounds. XXVI. Nucleophilic Displacement Reactions of Some Halogen-substituted Phenylcyclobutenones Marjorie C. Caserio, Howard E. Simmons Jr., A. Earl Johnson, and John D. Roberts Journal of the American Chemical Society 1960 82 (12), 3102-3106 DOI: 10.1021/ja01497a030
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61326
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 19:35
Last Modified:20 Oct 2015 19:35

Repository Staff Only: item control page