Issue 7, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

7-Oxanorbornene cycloadducts. X-Ray, molecular orbital and photoelectron spectroscopic study†

Mirjana Eckert-Maksić,*a   Nana Novak-Doumbouya,a   Rudolf Kiraljb  and  Biserka Kojić-Prodić‡b  

* Corresponding authors

a Laboratory for Physical Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Zagreb, Croatia

b Laboratory for Chemical and Biological Crystallography, Division of Physical Chemistry, Ruđer Bošković Institute, Zagreb, Croatia

Abstract

Structural (X-ray and MP2(fc)/6-31G*) features of 1,4∶5,8-diepoxynaphthalenes 1 and 2 are reported. The extent of endo bending of the olefinic hydrogens is estimated from the calculated structures and compared with the X-ray data. The computed out-of-plane angles are 7.6 and 6.8° in 1 and 2, respectively. Photoelectron spectroscopic data of diepoxynaphthalenes 1 and 2 and their higher analogue 3 are discussed and interpreted in terms of through-space and through-bond interaction of the oxygen lone pairs and their interactions with the olefinic π-orbital.

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Article information

DOI
https://doi.org/10.1039/B001267J
Article type
Paper
Submitted
15 Feb 2000
Accepted
16 May 2000
First published
15 Jun 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 1483-1487

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7-Oxanorbornene cycloadducts. X-Ray, molecular orbital and photoelectron spectroscopic study

M. Eckert-Maksić, N. Novak-Doumbouya, R. Kiralj and B. Kojić-Prodić, J. Chem. Soc., Perkin Trans. 2, 2000, 1483 DOI: 10.1039/B001267J

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