The first N,N′-ditosyl-substituted cyclic boron cation, stabilized by neighboring-group participation by two sulfonyl groups, and the alternative, stabilized by polar solvents

Tetrahedron Letters

Volumn 46, Issue 2, 2005, Pages 209-212

  Kiyooka, Syun Ichi ^a   Fujiyama, Ryoji ^a   Uddin, Md Khabir ^b   Goh, Kazuki ^a   Nagano, Yoshiya ^b   Fujio, Mizue ^b   Tsuno, Yuho ^b  

^a KOCHI UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

11B NMR; Boron cation; Structure characterization

Indexed keywords

2 BROMO 1,3 DITOSYL 1,3,2 DIAZABOROLIDINE; ANTIMONY DERIVATIVE; BORON DERIVATIVE; CHLORINE DERIVATIVE; FLUORINE DERIVATIVE; NITROGEN DERIVATIVE; OXYGEN; SILVER DERIVATIVE; SOLVENT; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ANALYTIC METHOD; ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 10044234917     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.068     Document Type: Article

References (22)

1. Y. Hayashi, J.J. Rohde, and E.J. Corey J. Am. Chem. Soc. 118 1996 5502 5503
2. E.J. Corey, T. Shibata, and T.W. Lee J. Am. Chem. Soc. 124 2002 3808 3809
3. S.-i. Kiyooka, R. Fujiyama, T. Kawai, H. Fujimoto, and K. Goh Tetrahedron Lett. 42 2001 4151 4153
4. S.-i. Kiyooka, H. Fujimoto, M. Mishima, S. Kobayashi, M.K. Uddin, and M. Fujio Tetrahedron Lett. 44 2003 927 930
5. M.K. Uddin, R. Fujiyama, S.-i. Kiyooka, M. Fujio, and Y. Tsuno Tetrahedron Lett. 45 2004 3913 3916
6. P. Kölle, and H. Nöth Chem. Rev. 85 1985 399 418
7. Cationic terminal borylenes: Os; G.J. Irvine, C.E.F. Rickard, W.R. Roper, A. Williamson, and L.J. Wright Angew. Chem., Int. Ed. 39 2000 948 950
8. Fe; D. Coombs, S. Aldridge, C. Jones, and D.J. Willock J. Am. Chem. Soc. 125 2003 6356 6357
9. Cr; H. Braunschweig, M. Colling, C. Hu, and K. Radacki Angew. Chem., Int. Ed. 42 2003 205 208
10. H. Nöth, B. Rasthofer, and S. Weber Z. Naturforsch., B: Anorg. Chem., Org. Chem. 39B 1984 1058 1068
11. J. Higashi, A.D. Eastman, and R.W. Parry Inorg. Chem. 21 1982 716 720
12. S. Courtenay, J.Y. Mutus, R.W. Schurko, and D.W. Stephan Angew. Chem., Int. Ed. 41 2002 498 501
13. C.K. Narula, and H. Nöth Inorg. Chem. 23 1984 4147 4152
14. E.J. Corey, C.-M. Yu, and S.S. Kim J. Am. Chem. Soc. 111 1989 5495 5496
15. 2, ppm): δ 21.8, 43.7, 128.1, 130.9, 147.0
16. F. London J. Phys. Radium (Paris) 8 1937 397
17. R. Ditchfield Mol. Phys. 24 1974 789
18. K. Wolinski, J.F. Hilton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251 8260
19. 2, ppm): δ 21.9, 44.1, 129.6, 131.8, 134.6, 148.6
20. 1a appears to be one of the structures that satisfy this need
21. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
22. Gaussian 98, Revision A.11: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh PA, 2002