- Turkish Journal of Chemistry
- Vol: 25 Issue: 1
- Synthesis and Structure of Systems Containing Pyramidalized and Strained Double Bond: An Investigati...
Synthesis and Structure of Systems Containing Pyramidalized and Strained Double Bond: An Investigation on the Cycloaddition Reactions of cisand trans-3,8-dicarbomethoxy-3,8-dihydroheptalene
Authors : Synthesis And Structure Of Systems Conta And
Pages : 123-133
View : 7 | Download : 6
Publication Date : 9999-12-31
Article Type : Makaleler
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 various dienophiles such as dimethyl acetylenedicarboxylate (DMAD), p-benzoquinone, maleic anhydride, tetracyanoethylene, naphtoquinone gave monoaddition products 15-23. Further addition of benzyne and dimethyl acetylenedicarboxylate to 18 resulted in the formation of the compounds syn-25 and syn-26 having pyramidalized double bonds. The addition of benzyne to 21 and the addition of dimethyl acetylenedicarboxylate to 21, 22 and 23 gave the anti configuration products anti-26, 27 and 28, respectively. X-ray structures of syn-25, syn-26 and anti-26 show the pyramidalized angles to be 16.5o, 19.9o and 8.0o, respectively.Keywords : Turk. J. Chem., 25, (2001), 123-133. Full text: pdf Other articles published in the same issue: Turk. J. Chem., vol.25, iss.1.