AN APPROACH TO FUNCTIONALIZED CUBANES - REGIOSELECTIVITIES AND FRONTIER MOLECULAR-ORBITAL ANALYSIS IN THE ADDITION OF DIMETHYL CYCLOBUTADIENE-1,2-DICARBOXYLATE TO QUINONES

Authors
MEHTA G VISWANATH MB JEMMIS ED SASTRY GN
Citation
G. Mehta et al., AN APPROACH TO FUNCTIONALIZED CUBANES - REGIOSELECTIVITIES AND FRONTIER MOLECULAR-ORBITAL ANALYSIS IN THE ADDITION OF DIMETHYL CYCLOBUTADIENE-1,2-DICARBOXYLATE TO QUINONES, Perkin transactions. 2, (3), 1994, pp. 433-436
Citations number
18
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Perkin transactions. 2 → ACNP
ISSN journal
03009580
Issue
3
Year of publication
1994
Pages
433 - 436
Database
ISI
SICI code
0300-9580(1994):3<433:AATFC->2.0.ZU;2-V
Abstract
4 + 2 Cycloaddition between dimethyl cyclobutadiene-1,2-dicarboxylate and benzoquinone, 4, gives 6, 7 and 8 in the ratio 15:4:1. Similarly n aphthoquinone. 5, furnishes 9, 10 and 11 in the ratio 11:1:2. Formatio n of symmetrical adducts is predominent in both cases. Irradiation of major adducts 6 and 9 results in a cascade of photorearrangements. Sem iempirical AM1 calculations are used to rationalize the regioselectivi ties.