Sequential Transition States and the Valley−Ridge Inflection Point in the Formation of a Semibullvalene
Two sequential transition states are calculated at the B3LYP/6-31G(d,p) level for the deazetization of 3b. The intrinsic reaction coordinate for loss of nitrogen passes through a transition state and then a valley−ridge inflection point and ultimately leads to the transition state for the Cope rearr...
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Published in | Organic letters Vol. 4; no. 19; pp. 3279 - 3282 |
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Format | Journal Article |
Language | English |
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United States
American Chemical Society
19.09.2002
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Abstract | Two sequential transition states are calculated at the B3LYP/6-31G(d,p) level for the deazetization of 3b. The intrinsic reaction coordinate for loss of nitrogen passes through a transition state and then a valley−ridge inflection point and ultimately leads to the transition state for the Cope rearrangement of semibullvalene 4b. The energetic and geometrical consequences are discussed. |
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AbstractList | [structure: see text] Two sequential transition states are calculated at the B3LYP/6-31G(d,p) level for the deazetization of 3b. The intrinsic reaction coordinate for loss of nitrogen passes through a transition state and then a valley-ridge inflection point and ultimately leads to the transition state for the Cope rearrangement of semibullvalene 4b. The energetic and geometrical consequences are discussed. Two sequential transition states are calculated at the B3LYP/6-31G(d,p) level for the deazetization of 3b. The intrinsic reaction coordinate for loss of nitrogen passes through a transition state and then a valley−ridge inflection point and ultimately leads to the transition state for the Cope rearrangement of semibullvalene 4b. The energetic and geometrical consequences are discussed. |
Author | Zhou, Chun Birney, David M |
Author_xml | – sequence: 1 givenname: Chun surname: Zhou fullname: Zhou, Chun – sequence: 2 givenname: David M surname: Birney fullname: Birney, David M |
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Cites_doi | 10.1021/ar00072a001 10.1021/ja00846a012 10.1021/ja010659k 10.1126/science.272.5267.1456 10.1021/ja01607a028 10.1039/tf9686400371 10.1007/BF00533485 10.1021/ja963551r 10.1021/j100377a021 10.1016/S0009-2614(02)00041-6 10.1021/ja00145a020 10.1021/ja025634f 10.1016/S0040-4020(01)87571-2 10.1021/ja00059a044 10.1021/ar00050a004 10.1021/ja016622h 10.1021/ja000531n 10.1021/ar50075a002 10.1002/jcc.10013 |
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References | Engel P. S. (ol026595fb00014/ol026595fb00014_1) 1983; 105 Toma L. (ol026595fb00005/ol026595fb00005_1) 2001; 42 Houk K. N. (ol026595fb00012/ol026595fb00012_1) 1995; 28 For (ol026595fb00008/ol026595fb00008_1) 1996; 118 Wenthold P. G. (ol026595fb00018/ol026595fb00018_1) 1996; 272 For (ol026595fb00011/ol026595fb00011_2) 2000; 122 Sauer J. (ol026595fb00001/ol026595fb00001_1) 2002; 791 González C. (ol026595fb00002/ol026595fb00002_2) 1990; 94 Fukui K. (ol026595fb00002/ol026595fb00002_1) 1981; 14 Frisch M. J. (ol026595fb00010/ol026595fb00010_1) 1998 Goldstein E. (ol026595fb00012/ol026595fb00012_2) 1996; 118 Becke A. D. (ol026595fb00009/ol026595fb00009_1) 1993; 98 Sannes K. A. (ol026595fb00019/ol026595fb00019_1) 1995; 117 Baken V. (ol026595fb00003/ol026595fb00003_2) 2001; 123 One (ol026595fb00007/ol026595fb00007_1) 1974; 61 Castaño O. (ol026595fb00003/ol026595fb00003_5) 2002; 23 Caramella P. (ol026595fb00005/ol026595fb00005_2) 2002; 124 Birney D. M. (ol026595fb00017/ol026595fb00017_1) 1997; 119 Hammond G. S. J. (ol026595fb00016/ol026595fb00016_1) 1955; 77 Mann D. J. (ol026595fb00003/ol026595fb00003_4) 2002; 124 Deazetization (ol026595fb00004/ol026595fb00004_1) 1993; 115 Birney D. M. (ol026595fb00015/ol026595fb00015_1) 1986; 42 Hariharan P. C. (ol026595fb00009/ol026595fb00009_2) 1973; 28 Birney D. (ol026595fb00012/ol026595fb00012_3) 2002; 124 Murrell J. N. (ol026595fb00006/ol026595fb00006_1) 1968; 64 Bartsch R. A. (ol026595fb00003/ol026595fb00003_1) 2001; 123 McIver J. W. (ol026595fb00006/ol026595fb00006_2) 1974; 7 For (ol026595fb00011/ol026595fb00011_1) 1997; 106 Hrovat D. A. (ol026595fb00013/ol026595fb00013_2) 2000; 122 Stanton R. E. (ol026595fb00006/ol026595fb00006_3) 1975; 97 Yamataka H. (ol026595fb00003/ol026595fb00003_3) 2002; 353 Jiao H. (ol026595fb00013/ol026595fb00013_1) 1997; 119 |
References_xml | – volume: 105 start-page: 6851 year: 1983 ident: ol026595fb00014/ol026595fb00014_1 publication-title: J. Am. Chem. Soc. contributor: fullname: Engel P. S. – volume: 14 start-page: 368 year: 1981 ident: ol026595fb00002/ol026595fb00002_1 publication-title: Acc. Chem. Res. doi: 10.1021/ar00072a001 contributor: fullname: Fukui K. – volume: 97 start-page: 3646 year: 1975 ident: ol026595fb00006/ol026595fb00006_3 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00846a012 contributor: fullname: Stanton R. E. – volume-title: Gaussian 98, revision A.6 year: 1998 ident: ol026595fb00010/ol026595fb00010_1 contributor: fullname: Frisch M. J. – volume: 123 start-page: 7486 year: 2001 ident: ol026595fb00003/ol026595fb00003_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja010659k contributor: fullname: Bartsch R. A. – volume: 272 start-page: 1459 year: 1996 ident: ol026595fb00018/ol026595fb00018_1 publication-title: Science doi: 10.1126/science.272.5267.1456 contributor: fullname: Wenthold P. G. – volume: 119 start-page: 5929 year: 1997 ident: ol026595fb00013/ol026595fb00013_1 publication-title: J. Am. Chem. Soc. contributor: fullname: Jiao H. – volume: 123 start-page: 134 year: 2001 ident: ol026595fb00003/ol026595fb00003_2 publication-title: J. Am. Chem. Soc. contributor: fullname: Baken V. – volume: 98 start-page: 5652 year: 1993 ident: ol026595fb00009/ol026595fb00009_1 publication-title: J. Chem. Phys. contributor: fullname: Becke A. D. – volume: 77 start-page: 338 year: 1955 ident: ol026595fb00016/ol026595fb00016_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01607a028 contributor: fullname: Hammond G. S. J. – volume: 64 start-page: 377 year: 1968 ident: ol026595fb00006/ol026595fb00006_1 publication-title: J. Trans. Faraday Soc. doi: 10.1039/tf9686400371 contributor: fullname: Murrell J. N. – volume: 28 start-page: 213 year: 1973 ident: ol026595fb00009/ol026595fb00009_2 publication-title: Theor. Chim. Acta doi: 10.1007/BF00533485 contributor: fullname: Hariharan P. C. – volume: 119 start-page: 4517 year: 1997 ident: ol026595fb00017/ol026595fb00017_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja963551r contributor: fullname: Birney D. M. – volume: 118 start-page: 6043 year: 1996 ident: ol026595fb00012/ol026595fb00012_2 publication-title: J. Am. Chem. Soc. contributor: fullname: Goldstein E. – volume: 94 start-page: 5523 year: 1990 ident: ol026595fb00002/ol026595fb00002_2 publication-title: J. Phys. Chem. doi: 10.1021/j100377a021 contributor: fullname: González C. – volume: 118 start-page: 4209 year: 1996 ident: ol026595fb00008/ol026595fb00008_1 publication-title: J. Am. Chem. Soc. contributor: fullname: For – volume: 353 start-page: 316 year: 2002 ident: ol026595fb00003/ol026595fb00003_3 publication-title: Chem. Phys. Lett. doi: 10.1016/S0009-2614(02)00041-6 contributor: fullname: Yamataka H. – volume: 117 start-page: 10092 year: 1995 ident: ol026595fb00019/ol026595fb00019_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00145a020 contributor: fullname: Sannes K. A. – volume: 124 start-page: 5099 year: 2002 ident: ol026595fb00012/ol026595fb00012_3 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja025634f contributor: fullname: Birney D. – volume: 42 start-page: 1570 year: 1986 ident: ol026595fb00015/ol026595fb00015_1 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)87571-2 contributor: fullname: Birney D. M. – volume: 115 start-page: 2437 year: 1993 ident: ol026595fb00004/ol026595fb00004_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00059a044 contributor: fullname: Deazetization – volume: 106 start-page: 1079 year: 1997 ident: ol026595fb00011/ol026595fb00011_1 publication-title: J. Chem. Phys. contributor: fullname: For – volume: 122 start-page: 10925 year: 2000 ident: ol026595fb00011/ol026595fb00011_2 publication-title: J. Am. Chem. Soc. contributor: fullname: For – volume: 42 start-page: 5080 year: 2001 ident: ol026595fb00005/ol026595fb00005_1 publication-title: Tetrahedron Lett. contributor: fullname: Toma L. – volume: 28 start-page: 81 year: 1995 ident: ol026595fb00012/ol026595fb00012_1 publication-title: Acc. Chem. Res. doi: 10.1021/ar00050a004 contributor: fullname: Houk K. N. – volume: 124 start-page: 1131 year: 2002 ident: ol026595fb00005/ol026595fb00005_2 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja016622h contributor: fullname: Caramella P. – volume: 791 start-page: 801 year: 2002 ident: ol026595fb00001/ol026595fb00001_1 publication-title: Eur. J. Org. Chem. contributor: fullname: Sauer J. – volume: 61 start-page: 3209 year: 1974 ident: ol026595fb00007/ol026595fb00007_1 publication-title: J. Chem. Phys. contributor: fullname: One – volume: 124 start-page: 3209 year: 2002 ident: ol026595fb00003/ol026595fb00003_4 publication-title: J. Am. Chem. Soc. contributor: fullname: Mann D. J. – volume: 122 start-page: 7460 year: 2000 ident: ol026595fb00013/ol026595fb00013_2 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja000531n contributor: fullname: Hrovat D. A. – volume: 7 start-page: 77 year: 1974 ident: ol026595fb00006/ol026595fb00006_2 publication-title: Acc. Chem. Res. doi: 10.1021/ar50075a002 contributor: fullname: McIver J. W. – volume: 23 start-page: 735 year: 2002 ident: ol026595fb00003/ol026595fb00003_5 publication-title: J. Comput. Chem. doi: 10.1002/jcc.10013 contributor: fullname: Castaño O. |
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Snippet | Two sequential transition states are calculated at the B3LYP/6-31G(d,p) level for the deazetization of 3b. The intrinsic reaction coordinate for loss of... [structure: see text] Two sequential transition states are calculated at the B3LYP/6-31G(d,p) level for the deazetization of 3b. The intrinsic reaction... |
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Title | Sequential Transition States and the Valley−Ridge Inflection Point in the Formation of a Semibullvalene |
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