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
Publication type: Journal Article
Publication date: 1990-01-31
scimago Q2
wos Q3
SJR: 0.491
CiteScore: 3.0
Impact factor: 1.8
ISSN: 0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Controlled 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 of 2 and 4 have been recorded. Comparison with the PE data of related systems, and with the result of ab initio STO-3G calculations, confirm the existence of significant through-bond interactions between the oxygen lone-pair orbitals n(CO) of the carbonyl functions and n(O) of the O(7) ether bridge.
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Röser K. et al. 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 // Helvetica Chimica Acta. 1990. Vol. 73. No. 1. pp. 1-12.
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Röser K., Carrupt P., Vogel P., Honegger E., Heilbronner E. 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 // Helvetica Chimica Acta. 1990. Vol. 73. No. 1. pp. 1-12.
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TY - JOUR
DO - 10.1002/hlca.19900730102
UR - https://doi.org/10.1002/hlca.19900730102
TI - 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
T2 - Helvetica Chimica Acta
AU - Röser, Karl
AU - Carrupt, Pierre-Alain
AU - Vogel, P.
AU - Honegger, Evi
AU - Heilbronner, Edgar
PY - 1990
DA - 1990/01/31
PB - Wiley
SP - 1-12
IS - 1
VL - 73
SN - 0018-019X
SN - 1522-2675
ER -
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@article{1990_Röser,
author = {Karl Röser and Pierre-Alain Carrupt and P. Vogel and Evi Honegger and Edgar Heilbronner},
title = {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},
journal = {Helvetica Chimica Acta},
year = {1990},
volume = {73},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/hlca.19900730102},
number = {1},
pages = {1--12},
doi = {10.1002/hlca.19900730102}
}
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Röser, Karl, et al. “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.” Helvetica Chimica Acta, vol. 73, no. 1, Jan. 1990, pp. 1-12. https://doi.org/10.1002/hlca.19900730102.