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Thermal Isomerization of 1,3‐Dipolar Cycloadducts of 3,4‐Dihydro‐β‐carboline 2‐Oxide
Author(s) -
Moriyama Satoshi,
Vallée Yannick
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199807)1998:7<1391::aid-ejoc1391>3.0.co;2-g
Subject(s) - isomerization , chemistry , oxide , nuclear magnetic resonance spectroscopy , photochemistry , methyl methacrylate , stereochemistry , organic chemistry , catalysis , polymerization , polymer
The thermal isomerization of the 1,3‐dipolar cycloadducts of 3,4‐dihydro‐β‐carboline 2‐oxide is studied using 1 H‐NMR spectroscopy. Stereoisomerizations of the cis or syn cycloadducts with dipolarophiles such as methyl crotonate, methyl cinnamate, and methyl methacrylate into the trans or anti cycloadducts are observed. On the other hand, regioisomerization of the 1‐substituted cycloadduct with nitroethylene into the 2‐substituted cycloadduct is also observed.