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Interaction between Oxygen Lone‐Pair Orbitals of Ether and α,β‐Unsaturated Ketone Functions in 3,5,6‐Trimethylidene‐7‐oxabicyclo[2.2.1]heptan‐2‐one and 3,6‐Dimethylidene‐7‐oxabicyclo[2.2.1]heptane‐2,5‐dione: A PE‐Spectroscopic Investigation

 

作者: Karl Röser,   Pierre‐Alain Carrupt,   Pierre Vogel,   Evi Honegger,   Edgar Heilbronner,  

 

期刊: Helvetica Chimica Acta  （WILEY Available online 1990）
卷期: Volume 73, issue 1  

页码: 1-12

 

ISSN:0018-019X

 

年代: 1990

 

DOI:10.1002/hlca.19900730102

 

出版商: WILEY‐VCH Verlag GmbH

 

数据来源: WILEY

 

摘要:

AbstractControlled ozonolysis of 2,3,5,6‐tetramethylidene‐7‐oxabicyclo[2.2.1]heptane (1) afforded 3,5,6‐trimethylidene‐7‐oxabicyclo[2.2.1]heptan‐2‐one (2). Ozonolysis of 2 gave a 1:1 mixture of 3,5‐dimethylidene‐7‐oxa‐bicyclo[2.2.1]heptane‐2,6‐dione (3) and 3,6‐dimethylidene‐7‐oxabicyclo[2.2.1]heptane‐2,5‐dione (4). The He(Iα) photoelectron (PE) spectra of2and4have been recorded. Comparison with the PE data of related systems, and with the result ofab initioSTO‐3G calculations, confirm the existence of significant through‐bond interactions between the oxygen lone‐pair orbitals n(CO) of the carbonyl

 

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