Naval Postgraduate School
Cyclopropane Ring Opening by Photolytically Generated Bromine Atoms
Article (805.2Kb)Abstract
Bromine atoms, generated by irradiation by a mercury lamp bearing a filter to assure that only wavelengths
>310 nm passed, were permitted to react with a series of 1,2-diarylcyclopropanes in carbon tetrachloride solution.
The major product in all cases (>80%) was the 1,3-dibromo-1,3-diarylpropane. Kinetic data at approximately
10ˉ³M gave a rate expression dBr₂/dt = -k(cyclopropane)(bromine)¹′². A Hammett treatment of the data gave p
= -0.5 for both the cis series and the trans series. Synthesis of several possible minor products and their comparison
with the reaction mixture by TLC is reported. Possible reactions such as induced isomerization are thus eliminated
from consideration.
Description
The article of record as published may be found at http://dx.doi.org/10.1021/jo00909a001
Rights
This publication is a work of the U.S. Government as defined in Title 17, United States Code, Section 101. Copyright protection is not available for this work in the United States.Collections
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