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

Date

2001-01-01

Author

Saracoglu, N
Menzek, A
Balcı, Metin

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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 degrees, 19.9 degrees and 8.0 degrees respectively.

Subject Keywords

Cycloheptatriene-norcaradiene equilibrium, Alkenes, Benzyne

URI

https://hdl.handle.net/11511/52788

Journal

TURKISH JOURNAL OF CHEMISTRY

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Graduate School of Natural and Applied Sciences, Article

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Citation Formats

N. Saracoglu, A. Menzek, and M. Balcı, “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, pp. 123–133, 2001, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/52788.