Synthesis and Structure of Systems Conta And

9393

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

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.

Anahtar Kelimeler:

Turk. J. Chem., 25, (2001), 123-133. Full text: pdf Other articles published in the same issue: Turk. J. Chem., vol.25, iss.1.

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

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.,

Turkish Journal of Chemistry-Cover

ISSN: 1300-0527
Yayın Aralığı: 6
Yayıncı: TÜBİTAK

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