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Diels-alder reactions of pyrano[3,4-b]indol-3-ones with olefinic compounds : Synthesis of (1,2-dihydro)carbazoles

✍ Scribed by P. Van Doren; D. Vanderzande; S. Toppet; G. Hoornaert

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 701 KB
Volume: 45
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89146-8

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✦ Synopsis

The role of the substitution pattern on the stability of the obtained 1.2-dihydreearbazolee is interpreted In terms of electronic and steric effects on the aromatization to the corresponding carbazoles. CH and 2-CHb bonds, a small coupling constant of 1,6 Hz is observed. A dihedral angle of about 26' between 1-dH and' 2-CH, and a nearly orthogonal poaltion of 2-H, towards the 3,4-Vinyl bond eXphinS the 3JlH_2Ha value of 7.6 Hz and the long range between 2-H, and 4-H.

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