Mechanism of pyridyne formation from halopyridines |
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| Affiliation: | 1. Department of Chemistry, College of Engineering and Physical Sciences, Khalifa University, P.O Box: 127788, Abu Dhabi, United Arab Emirates;2. Materials and Surface Core Labs, Khalifa University, P.O. Box 127788, Abu Dhabi, United Arab Emirates;3. Electron Microscopy Core Labs, Khalifa University, P.O. Box 127788, Abu Dhabi, United Arab Emirates;4. Department of Chemical Engineering, Indian Institute of Technology Delhi, New Delhi, 110016, India;5. Mechanical and Nuclear Engineering Department, College of Engineering and Physical Sciences, Khalifa University, P.O Box: 127788, Abu Dhabi, United Arab Emirates;1. Department of Chemistry, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh;2. Department of Agricultural Chemistry, Sher-e-Bangla Agricultural University, Sher-e-Bangla Nagar, Dhaka 1207, Bangladesh;3. Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, UK;4. Department of Chemistry, King''s College London, Britannia House, 7 Trinity Street, London SE1 1DB, UK;5. Department of Chemistry, University of North Texas, 1155 Union Circle, Box 305070, Denton, TX 76203, USA;6. Inorganic Research Group, Chemical Physics, Center for Chemistry and Chemical Engineering, Lund University, Post Box 124, SE-22100, Lund, Sweden;1. Department of Chemistry, Iran University of Science and Technology, Narmak, Tehran 16846-13114, Iran;2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran;3. Department of Tuberculin & Mallein, Razi Vaccine & Serum Research Institute, Agricultural Research Education and Extension Organization (AREEO), Karaj, Iran;4. School of Chemistry, College of Science, University of Tehran, Tehran PO Box 14155-6455, Iran;1. Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang, 318000, PR China;2. Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, PR China;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, PR China |
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| Abstract: | Rates of hydrogen-deuterium exchange of 3-chloro- and 3,5-dichloropyridine in MeOD-MeONa were studied. Deuterodeprotonation of 3-chloropyridine at 110·2° is 53 times faster at H-4 than at H-2. At 75° the value of the ortho chloro rate factor for exchange is 800; the para nitrogen rate factor is 3000. Interrupted dehydrohalogenation of 3-chloropyridine-2 or 4-d and 3-iodopyridine-4d in NH3NaNH2 to give 3,4-pyridyne results in no detectable loss of label at 2 in the chloropyridine but reduction and enrichment of 4-d in the chloro and iodo compounds, respectively. Results are interpreted in terms of the reactions of halopyridyl anions. |
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