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

NURULLAH SARAÇOĞLU
ABDULLAH MENZEK
METİN BALCI

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 16.5^o, 19.9^o and 8.0^o, respectively.

DOI

-

First Page

123

Last Page

133

Recommended Citation

SARAÇOĞLU, N, MENZEK, A, & BALCI, M (2001). 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. Turkish Journal of Chemistry 25 (1): 123-133. https://doi.org/-