ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The condensation of methyl-2-thienyl-, and phenyl-2-thienyl-ketones with dimethyl succinate in the presence of potassium t-butoxide or sodium hydride gave predominantly the (E)-half-estersi.e., CO2CH3 group and thiophene ring in trans-position. The nomenclature of cis/trans isomers used herein follows the IUPAC 1968 Tentative Rules, Section E, Fundamental Stereochemistry, J. org. Chemistry 35, 2849 (1970). See also: J. E. BLACKWOOD, C. L. GLADYS, K. L. LOENING, A. E. PETRARCA, and J. E. RUSH, J. Amer. chem. Soc. 90, 510 (1968); Introduction to Subject Index of Chem. Abstr. 66 (1963). 1a and 1d, which were cyclised to benzothiophene derivatives 2a and 2e, respectively. Methanolysis of the derived anhydrides 3a and 3 b led to the formation of the half-esters 1c and 1f. The (E)-dibasic acids 1b and 1e were converted by concentrated sulphuric acid to the lactones 4a and 4b. The methoxy-acid 2h gave upon such treatment the fluorenone derivative 5.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19733150215
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