X-Ray Structural Analysis of Ester and Ether Derivatives of 4,5-endo,endo-9,10-Dimethanonaphthalene-11-ol: Evidence for π–σCO* Participation in the Ground State

Wesley Jackson; Jonathan M. White

doi:10.1071/CH08402

RESEARCH ARTICLE

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X-Ray Structural Analysis of Ester and Ether Derivatives of 4,5-endo,*endo-9,10-Dimethanonaphthalene-11-ol: Evidence for π–σ_CO Participation in the Ground State

Wesley Jackson ^A and Jonathan M. White ^A ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Bio-21 Institute, University of Melbourne, Parkville, Vic. 3010, Australia.

^B Corresponding author. Email: whitejm@unimelb.edu.au

Australian Journal of Chemistry 61(12) 956-961 https://doi.org/10.1071/CH08402
Submitted: 24 September 2008 Accepted: 9 October 2008 Published: 10 December 2008

Abstract

Application of the variable oxygen probe to the polycyclic alcohol 11 and its crystalline ester and ether derivatives provides evidence for a weak interaction between the neighbouring homo-allylic π-system and the C–OR bond; there is no evidence for interaction with the remote π-system. Analysis of the carbon–carbon bond distances in 11–14 reveals structural effects consistent with the manifestation of one of the two possible retro-Diels–Alder reactions in the ground state.

References

X-Ray Structural Analysis of Ester and Ether Derivatives of 4,5-endo,endo-9,10-Dimethanonaphthalene-11-ol: Evidence for π–σCO* Participation in the Ground State

Abstract

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X-Ray Structural Analysis of Ester and Ether Derivatives of 4,5-endo,*endo-9,10-Dimethanonaphthalene-11-ol: Evidence for π–σ_CO Participation in the Ground State