Original scientific paper

Bromolactone Structures derived from Cyclohex-3-ene-1,1-dicarboxylic Acids and Syntheses of Multifunctional Cyclohexanecarboxylic Acids

Vera Turjak-Zebić ; Laboratory of Stereochemistry and Natural Products
Vinko Škarić ; Laboratory of Stereochemistry and Natural Products
Živa Ružić-Toroš ; X-ray Laboratory, »Ruđer Bošković" Institute, 41001 Zagreb, Croatia, Yugoslavia
Biserka Kojić-Prodić ; X-ray Laboratory, »Ruđer Bošković" Institute, 41001 Zagreb, Croatia, Yugoslavia

Abstract

It was shown that the bromolactonization of 4-cyanocyclohex-
-3-ene-l,1-dicarboxylic acid (10) in water or aqueous NaHC03
proceeded to t-4-bromo-c-a-cyano-c-s- hydroxycyclohexane- r-le,
1-dicarboxylic acid (13)via the intermediate c-4-bromo-t-4-cyano-
-6-oxabicyclo[3.2.1]octan-7-one-r-1-carboxylic acid (11).In contrast
to this finding, 4-carbamoylcyclohex-3-ene-1,1-dicarboxylic acid
(19)yielded only c-4-bromo-t-4-carbamoyl-6-oxabicyclo[3.2.1]octan-
-7-one-r-1-carboxylic acid (20) by treatment with bromine in
aqueous NaHC03. The syntheses of 4-cyano-(25) and 4-carbamoyl-
-(26)-t-3,4-oxiranecyclohexane-r-le,1-dicarboxylate are also described. The structures and relative configurations of methyl c-4-
-bromo-t-4-cyano-6-oxa bicyclo[3.2.1]octan-7-one-r-T-carboxy late
(12), prepared from 11, and dimethyl c-3-benzoxy-t-4-bromo-c-4-
-cyanocyclohexane-r-le,l-dicarboxylate (15), prepared from 13,
were determined by X-ray analyses, confirmed also by lH-NMR
and lsC-NMR spectroscopies.

Keywords

Hrčak ID:

177384

URI

https://hrcak.srce.hr/177384

Publication date:

20.6.1986.

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