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Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/3300

Title: Grignard reactions on ortho dicarboxylic arene derivatives. Synthesis of 1,3-dithienylisothianaphthene compounds
Authors: Kiebooms, RHL
ADRIAENSENS, Peter
VANDERZANDE, Dirk
GELAN, Jan
Issue Date: 1997
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY, 62(5). p. 1473-1480
Abstract: 1,3-Dithienylisothianaphthene (10a) is obtained through ring closure of 1,2-dithienoylbenzene (7a). The synthesis of 7a has been accomplished based on a Grignard reaction by adding 2-thiophene-magnesium bromide to 1,2-di(S-(2-pyridinyl)) benzenedithioate (6b) to obtain 7a in a yield of 95%. The use of 6b avoids the formation of the corresponding 3,3-dithienyl-3H-isobenzofuran-1(3H)-one (dithienylphthalide, 8). The same procedure is applied to obtain 1,3-dithienyl-4,5,6,7-tetradeuterioisothianaphthene (10b) and 1,3-dithienyl-4,5,6,7-tetrafluoroisothianaphthene (10c). The synthesis of the 2,3-dithienoylpyridine (12a), 3,4-dithienoylpyridine (12b), and 2,3-dithienoylpyrazine (12c) however fails. The presence of nitrogen in the central ring system influences the result of the Grignard reaction. Possibly the free electron pair of the nitrogen interferes with the formation of a stable six-membered ring intermediate which is essential for the diketone formation.
Notes: UNIV LIMBURG,INST MAT RES IMO,DIV CHEM,B-3590 DIEPENBEEK,BELGIUM.
URI: http://hdl.handle.net/1942/3300
DOI: 10.1021/jo9604402
ISI #: A1997WM75600039
ISSN: 0022-3263
Type: Journal Contribution
Appears in Collections: Research publications

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