Synthesis and structure of systems containing pyramidalized and strained double bond: An investigation on the cycloaddition reactions of cis-and trans-3,8-dicarbomethoxy-3,8-dihydroheptalene

Authors
Saracoglu, N Menzek, A Balci, M
Citation
N. Saracoglu et al., Synthesis and structure of systems containing pyramidalized and strained double bond: An investigation on the cycloaddition reactions of cis-and trans-3,8-dicarbomethoxy-3,8-dihydroheptalene, TURK J CHEM, 25(1), 2001, pp. 123-133
Citations number
16
Categorie Soggetti
Chemistry
Journal title
TURKISH JOURNAL OF CHEMISTRY
ISSN journal
13000527 → ACNP
Volume
25
Issue
1
Year of publication
2001
Pages
123 - 133
Database
ISI
SICI code
1300-0527(2001)25:1<123:SASOSC>2.0.ZU;2-2
Abstract
The cycloaddition reactions of cis-3,8-dicarbomethoxy-3,8-dihydroheptalene cis-2 and trans-3,8-dicarbomethoxy-3,8-dihydroheptalene trans-2 with variou s dienophiles such as dimethyl acetylenedicarboxylate (DMAD), p-benzoquinon e. maleic anhydride, tetracyanoethylene, naphtoquinone gave monoaddition pr oducts 15-23. Further addition of benzyne and dimethyl acetylenedicarboxyla te to 18 resulted in the formation of the compounds syn-25 and syn-26 havin g pyramidalized double bonds. The addition of benzyne to 21 and the additio n of dimethyl acetylenedicarboxylate to 21, 22 and 23 gave the anti configu ration products anti-26, 27 and 28: respectively. X-ray structures of syn-2 5, syn-26 and anti-26 show the pyramidalized angles to be 16.5 degrees, 19. 9 degrees and 8.0 degrees respectively.