Oxidation of pyrrole α-methyl to methoxymethyl with ceric triflate

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 315-318

  Thyrann, Thomas ^a   Lightner, David A ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 0030069572     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02161-2     Document Type: Article

References (19)

1. Thyrann, T.; Lightner, D.A. Tetrahedron Lett. 1995, 36, 4345-4348.
2. Paine, J.B. III; Dolphin, D. Can. J. Chem. 1976, 54, 411-414.
3. Molander, G.A. Chem. Rev. 1992, 92, 29-68.
4. Ho, T.L. Synthesis, 1973, 347-354.
5. Imamoto, T.; Koide, Y.; Hiyama, S. Chem. Lett. 1990, 1445-1446.
6. 3) δ: 8.52 (q), 10.28 (q), 14.54 (q), 57.98 (q), 59.71 (q), 65.63 (t), 118.4 (s), 118.5 (s), 127.0 (s), 129.2 (s), 161.6 (s) ppm.
7. (b) Eisner, U.; Gore, P.H. J. Chem. Soc., 1958, 922-927.
8. 3) δ: 10.17 (q), 14.54 (q), 15.62 (q), 17.09 (t), 58.00 (q), 59.69 (q), 65.58 (t), 118.5 (s), 125.1 (s), 124.4 (s), 128.9 (s), 161.1 (s) ppm.
9. (b) Fischer, H.; Adler, E. Z. Physiol. Chem. 1931, 197, 237-280.
10. 5 (297.35): C, 60.59; H, 7.80; N, 4.71. Found: C, 60.83; H, 7.90; N, 4.76.
11. 3 (197.23): C, 60.90; H, 7.67; N, 7.10 Found: C, 60.82; H, 7.75; N, 7.10.
12. 3) δ: 12.37 (q), 14.42 (q), 30.64 (q), 59.11 (q), 60.24 (q), 68.86 (t), 118.7 (s), 122.3 (s), 128.4 (s), 139.8 (s), 161.1 (s), 195.0 (s) ppm.
13. (b) Rumyantseva, V.D.; Mironov, A.F.; Evstigneeva, R.P. Zh. Obshch. Khim., 1973, 43, 1611-1616.
14. 3) δ: 8.76 (q), 10.61 (q), 14.44 (q), 23.22 (t), 59.81 (t), 117.3 (s), 117.8 (s), 127.5 (s), 129.6 (s), 162.1 (s) ppm.
15. (b) Fischer, H.; Walach, B. Ann. 1926, 450, 109-132.
16. 3) δ: 10.40 (q), 14.51 (q), 15.30 (q), 17.24 (t), 23.16 (t), 59.76 (t), 118.2 (s), 124.2 (s), 127.0 (s), 128.6 (s), 161.8 (s) ppm.
17. (b) Fischer, H.; Halbig, P. Ann. 1926, 448, 193-204.
18. 3) δ: 10.54 (q), 14.54 (q), 13.39 (t), 22.72 (t), 34.61 (t), 51.62 (q), 59.69 (t), 118.7 (s), 120.3 (s), 126.7 (s), 130.1 (s), 161.5 (s), 173.7 (s) ppm
19. (b) Miranov, A.F.; Ovsepyan, T.R.; Evstigneeva, R.P.; Preobrazhenskii, N.A. Zh. Obshch. Khim. 1965, 35, 324-328.