A Caltech Library Service

Small-Ring Compounds. XXV. Phenylcyclobutadienoquinone and Related Compounds

Smutny, Edgar J. and Caserio, Marjorie C. and Roberts, John D. (1960) Small-Ring Compounds. XXV. Phenylcyclobutadienoquinone and Related Compounds. Journal of the American Chemical Society, 82 (7). pp. 1793-1801. ISSN 0002-7863.

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

Use this Persistent URL to link to this item:


Thermal addition of phenylacetylene to trifluorochloroethylene and tetrafluoroethylene followed by hydrolysis of either product with concentrated sulfuric acid has led to the formation of phenylcyclobutene-1,2-dione(phenylcyclobutadienoquinone). This compound proved to be quite stable and displayed some unusual properties. A number of its substitution products have been prepared and their properties are described. Of these, 4-hydroxy-3-phenylcyclobutene-1,2-dione was of special interest in being a remarkably strong acid with pK_a of 0.37. The stability of phenylcyclobutadienoquinone and the acid strength of the 4-hydroxy derivative are discussed and correlated with delocalization energies calculated by the LCAO method.

Item Type:Article
Related URLs:
URLURL TypeDescription
Additional Information:© 1960 American Chemical Society. Received August 10, 1959. Supported in part by the National Science Foundation; presented in part at the XIV National Organic Chemistry Symposium of the American Chemical Society, Lafayette. Ind., June, 1955.
Funding AgencyGrant Number
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry2484
Issue or Number:7
Record Number:CaltechAUTHORS:20151020-141340312
Persistent URL:
Official Citation:Small-Ring Compounds. XXV. Phenylcyclobutadienoquinone and Related Compounds Edgar J. Smutny, Marjorie C. Caserio, and John D. Roberts Journal of the American Chemical Society 1960 82 (7), 1793-1801 DOI: 10.1021/ja01492a061
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61338
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 21:48
Last Modified:03 Oct 2019 09:06

Repository Staff Only: item control page