Substituent effects on the transannular ring closure of 2,4-cyclooctadienones to 5,5-fused ring systems: an AM1 study

Date

2002-04-01

Author

Zora, Metin

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Substituent effects on the transannular ring closure of 2,4-cyclooctadienones to 5,5-fused ring systems were theoretically investigated by using AM1 method at the restricted HF level. As anticipated by elementary considerations, it was found that electron-donating substituents at positions 2 and 4 of cyclooctadienone lower the activation barrier, and make the transannular cyclization feasible. Substituents elsewhere on the ring including position 3 do not have a significant effect on the rearrrangement, their influence being mainly steric.

Subject Keywords

Physical and Theoretical Chemistry, Biochemistry, Condensed Matter Physics

URI

https://hdl.handle.net/11511/52321

Journal

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM

DOI

https://doi.org/10.1016/s0166-1280(01)00800-4

Collections

Department of Chemistry, Article

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Citation Formats

M. Zora, “Substituent effects on the transannular ring closure of 2,4-cyclooctadienones to 5,5-fused ring systems: an AM1 study,” JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, pp. 233–239, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/52321.