Reaction of ambident dianions with oxalic acid dielectrophiles - Effect of the heteroatoms of the dinucleophile on the regiochemistry of cyclization

European Journal of Organic Chemistry

Volumn , Issue 7, 1998, Pages 1467-1470

  Langer, Peter ^a   Wuckelt, Jörg ^a   Döring, Manfred ^a   Beckert, Rainer ^a  

^a NONE

Author keywords

Ambident dianions; C C coupling; Heterocycles; Oxalyl dielectrophiles; Regioselectivity

Indexed keywords

EID: 0001435342     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199807)1998:7<1467::AID-EJOC1467>3.0.CO;2-H     Document Type: Article

References (35)

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28. The structures were generated and the energies were subsequently minimized using the MM+ force field which is implemented in release 3.0 of HyperChem®, MM+ supplements the standard MM2 parameters (N. L. Allinger, J. Am. Chem. Soc. 1977, 99, 8127-8134 ). All input geometries were taken from the molecule editor and optimized using the Polak-Ribiere algorithm. Non-bonded electrostatic interactions were calculated as bond dipoles without cut-offs. The minima obtained from the search were further optimized using the AMI wavefunction (M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909) and the RHF approximation.
29. The structures were generated and the energies were subsequently minimized using the MM+ force field which is implemented in release 3.0 of HyperChem®, MM+ supplements the standard MM2 parameters (N. L. Allinger, J. Am. Chem. Soc. 1977, 99, 8127-8134 ). All input geometries were taken from the molecule editor and optimized using the Polak-Ribiere algorithm. Non-bonded electrostatic interactions were calculated as bond dipoles without cut-offs. The minima obtained from the search were further optimized using the AMI wavefunction (M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909) and the RHF approximation.
30. The dianion of phenylacetone was reported to be attacked by monofunctional alkyl halides at the methine rather than at the methylene site: G. B. Trimitsis, J M. Hinkley, R. TenBrink, A. L. Faburada, M. Anderson, M. Poli, B. Christian, G. Gustafson, J. Erdman, D. Rop. J. Org. Chem. 1983, 48, 2957-2962.
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33. For reactions of BTIOC with monoanions, see [19a] J. Wuckelt, M. Döring, P. Langer, R. Beckert, H. Görls, Tetrahedron Lett. 1997, 5269-5272. [19b] J. Wuckelt, M. Döring, P, Langer, H. Görls, R. Beckert, Tetrahedron Lett. 1998, 1135-1138.
34. For reactions of BTIOC with monoanions, see [19a] J. Wuckelt, M. Döring, P. Langer, R. Beckert, H. Görls, Tetrahedron Lett. 1997, 5269-5272. [19b] J. Wuckelt, M. Döring, P, Langer, H. Görls, R. Beckert, Tetrahedron Lett. 1998, 1135-1138.
35. For reactions of BTIOC with monoanions, see [19a] J. Wuckelt, M. Döring, P. Langer, R. Beckert, H. Görls, Tetrahedron Lett. 1997, 5269-5272. [19b] J. Wuckelt, M. Döring, P, Langer, H. Görls, R. Beckert, Tetrahedron Lett. 1998, 1135-1138.