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

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Zora M., Ozkan K.

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, vol.583, pp.233-239, 2002 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 583
• Publication Date: 2002
• Doi Number: 10.1016/s0166-1280(01)00800-4
• Journal Name: JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.233-239
• Middle East Technical University Affiliated: Yes

Abstract

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. (C) 2002 Elsevier Science B.V. All rights reserved.