Formation of 2-substituted Iodobenzenes from Iodobenzene via Benzyne and Ate Complex Intermediates

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1973-1975

  Tripathy, Sasmita ^a   LeBlanc, Richard ^a   Durst, Tony ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000416037     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991129k     Document Type: Article

References (10)

1. Dougherty, C. M.; Olofson, R. A. J. Am. Chem. Soc. 1973, 95, 581.
2. Fitzgerald, J. J.; Drysdale, N. E.; Olofson, R. A. J. Org. Chem. 1992, 57, 7122.
3. LeBlanc, R. M.Sc. Thesis, University of Ottawa, 1999.
4. 22N 343.0798, found 343.0788. The observation that the methyl groups in 1 occur as two singlets (1:1 ratio) indicates a significant barrier to rotations around the N-aryl bond. Molecular mechanics calculations show that the barrier to ring flipping/nitrogen inversion is approximately 41 kcal/mol. In compound 2, a single peak is observed for the four methyl groups.
5. 23N 217.1831, found 217.1816.
6. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Reich, H. J.; Reich, I. L.; Phillips, N. H. J. Am. Chem. Soc. 1985, 107, 4101.
7. Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444. Reich, H. J.; Reich, I. L.; Phillips, N. H. J. Am. Chem. Soc. 1985, 107, 4101.
8. 13C NMR data.
9. 17OI 348.0226, found 348.0223.
10. 4I 362.0015, found 362.0027.