The Lewis acid-promoted reactions of o-phthalaldehyde with trialkyl phosphites: Formation of 1-dialkoxyphosphorylisobenzofuran

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5963-5966

  Yamana, Kenji ^a   Nakano, Hirofumi ^a  

^a AICHI UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; ISOBENZOFURAN DERIVATIVE; NAPHTHALENE DERIVATIVE; PHOSPHITE; PHTHALALDEHYDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0030581341     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01288-9     Document Type: Article

References (12)

1. 1. Rickborn, B. Adv. Theor. Interesting Mol. 1989, 1, 1-134 and references cited therein.
2. 2. Forsey, S. P.; Rajapaksa, D.; Taylor, N. J.; Rodrigo, R. J. Org. Chem. 1989, 54, 4280-4290; Pelter, A.; Ward, R. S; Qianrong, L.; Pis, J. Tetrahedron Asymmetry 1994, 5, 909-920; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495-3498; Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938-3939.
3. 2. Forsey, S. P.; Rajapaksa, D.; Taylor, N. J.; Rodrigo, R. J. Org. Chem. 1989, 54, 4280-4290; Pelter, A.; Ward, R. S; Qianrong, L.; Pis, J. Tetrahedron Asymmetry 1994, 5, 909-920; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495-3498; Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938-3939.
4. 2. Forsey, S. P.; Rajapaksa, D.; Taylor, N. J.; Rodrigo, R. J. Org. Chem. 1989, 54, 4280-4290; Pelter, A.; Ward, R. S; Qianrong, L.; Pis, J. Tetrahedron Asymmetry 1994, 5, 909-920; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495-3498; Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938-3939.
5. 2. Forsey, S. P.; Rajapaksa, D.; Taylor, N. J.; Rodrigo, R. J. Org. Chem. 1989, 54, 4280-4290; Pelter, A.; Ward, R. S; Qianrong, L.; Pis, J. Tetrahedron Asymmetry 1994, 5, 909-920; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495-3498; Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938-3939.
6. 3. Haddadin, M. J.; Agha, B. J.; Tabri, R. F. J. Org. Chem. 1979, 44, 494-497.
7. 4. A solution of endo-adduct 5a in tetrachloroethane at 140 °C for 60 h in the presence of N-phenylmaleimide gave a mixture of 5a and 6a (60:40).
8. 3, 400 MHz) δ=3.23 (1H, d, J=6.7 Hz), 3.24 (1H, d, J=6.7 Hz), 3.85 (3H, d, J=11.0 Hz), 3.95 (3H, d, J=10.9 Hz), 5.95 (1H, d, J=1.0 Hz), 7.31-7.50 (7H, m), 7.63-7.65 (1H, m). The structure of 5a was finally determined by single crystal X-ray analysis. The results will be reported in full paper.
9. 6. Naito, K.; Rickborn, B. J. Org. Chem. 1980, 45, 4061-4062.
10. 3
11. 8. Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415-430; Brill, T. B.; Landon, S. J. Chem. Rev. 1984, 84, 577-585.
12. 8. Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415-430; Brill, T. B.; Landon, S. J. Chem. Rev. 1984, 84, 577-585.