Re: ORGLIST - orglist Digest - V01 #90/Michael Lynch

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From: Jacob Zabicky (zabicky$##$
Date: Tue Feb 03 1998 - 02:47:30 EST

>.... The reference I
>have gives a procedure to chlorinate the mono acid (which is simpler and
>faster than the one for the diacid) but it gives a mixture of the 2- and 3-
>chlorinated acids. My question is (finally) if I dehydorchlorinate the
>2-chlorocyclobutanecarboxylic acid will the proton on the #1 carbon be removed
>to form 1-cyclobutenecarboxylic acid or will it still form the product I want
>2-cyclobutenecarboxylic acid. 3-chlorocyclobutanecarboxylic acid is the major
>isomer formed but it would be nice if I could skip the step to seperate the
>isomers before I dehydrochlorinate the acid.

Dear Michael,

Personally I would expect that both the 3-chloro and the 2 chloro isomers
will yield the same product. But to be careful, if you get a substantial
amount of the chloro isomers, take a little part of it and try to carry out
the elimination. NMR of the product will probably tell you if you succeeded
in your endeavor. If not you'll have to separate the stuff.

Good luck

Prof. Jacob Zabicky Tel. 972-7-6461271/6461062/6472754
Institutes for Applied Research Fax. 972-7-6472969
Ben-Gurion University of the Negev Private: POB 12366 Beer-Sheva 84836
POB 653, Beer-Sheva 84105, ISRAEL Tel. 972-7-6496792


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