Singlet oxygenation of 1-aminomethyl-1-tert-butyl-2-methoxy-2-(3-methoxyphenyl)ethylenes: Marked effect of allylic nitrogen on the reaction pathways and chemoselectivity

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8191-8194

  Matsumoto, Masakatsu ^a   Kitano, Yushikazu ^b   Kobayashi, Hisako ^b   Ikawa, Hiroshi ^b  

^a KANAGAWA UNIVERSITY   (Japan)

^b FUJIREBIO INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; PEROXIDE;

ARTICLE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 0030569276     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01858-8     Document Type: Article

References (25)

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14. c) Organic Peroxide; Ando, W.; Wiley, New York, 1992.
15. 3) δ 1.47 9s, 9H), 2.13-2.41 (m, 2H), 2.59-2.87 (m, 2H), 3.02 (s, 3H), 3.80 (s, 3H), 5.86 (s, 1H), 6.78-6.97 (m, 3H), 7.21 (t, J = 8.0 Hz, 1H), and 9.87 (s, 1H) ppm.
16. 11. Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1995, 36, 4291-4294.
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24. +, 0.5), 332 (3), 317 (10), 279 (12), 231 (23), 201 (52), 166 (85), and 135 (100).
25. 16. Considering an interaction as in (T-3), the temperature effect observed for 1 1 is likely accounted for by a rotational isomerism of a trigonal flame of an amide function around an axis of N-C (allylic carbon). For a N-alkyl analogue of 7 bearing N-neopentyl, NMR analysis showed that it exists as a mixture of two rotamers even at room temperature, though they could not be unfortunately separated at present.