2,3-Bis(diphenylphosphynyl)-1,3-butadiene via a double [2,3]-sigmatropic rearrangement. A reinvestigation of the reaction of 2-butyne-1,4-diol with chlorodiphenylphosphine |
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| Affiliation: | 1. Department of Applied Chemistry and Biotechnology, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 7000005, Japan;2. Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of the Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan City, Hunan Province 411201, China;1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan;2. Katayama Chemical Industries Co., Ltd., 26-22, 3-Chome, Higasinaniwa-cho, Amagasaki, Hyogo 660-0892, Japan;3. Center for Education and Research in Agricultural Innovation, Faculty of Agriculture, Saga University, 152-1 Shonan-cho, Karatsu, Saga 847-0021, Japan;4. National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1, Higashi, Tsukuba, Ibaraki 305-8565, Japan;1. Department of Chemistry and Chemical Biology, Rutgers University, Piscataway, NJ 08854, USA;2. College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473061, PR China;1. Departamento de Química, Universidade Federal de São Carlos, Rod. Washington Luís, km 235 – SP-310, CEP 13565-905 São Carlos, SP, Brazil;2. Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador São-carlense, 400, CEP 13566-590 São Carlos, SP, Brazil;3. Leibniz-Institut für Katalyse an der Universität Rostock e.V., A.-Einstein-Str. 29a, 18059 Rostock, Germany;4. Faculdade de Ciências Integradas do Pontal, Universidade Federal de Uberlândia, Rua vinte, 1600, CEP 38304-402 Ituiutaba, MG, Brazil;1. Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan;2. Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan |
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| Abstract: | Contrary to previous reports, the reaction of 2-butyne-1,4-diol with chlorodiphenylphosphine yields 2,3-bis(diphenylphosphinyl)-1,3-butadiene 3 instead of the 1,4-isomer. The structure of the product has been elucidated from 1H, 13C and 31P-NMR spectroscopic data. |
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