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, Rafael ADRIAENSENS, Peter VANDERZANDE, Dirk GELAN, Jan |
Issue Date: | 1997 | Publisher: | AMER CHEMICAL SOC | Source: | 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. | Document URI: | http://hdl.handle.net/1942/3300 | DOI: | 10.1021/jo9604402 | ISI #: | A1997WM75600039 | Type: | Journal Contribution |
Appears in Collections: | Research publications |
Show full item record
SCOPUSTM
Citations
46
checked on Sep 3, 2020
WEB OF SCIENCETM
Citations
46
checked on Oct 12, 2024
Page view(s)
10
checked on Jun 13, 2022
Google ScholarTM
Check
Altmetric
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.