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Small and Medium Rings, 79 1) 4‐Azatetracyclo[3.3.0.0 2,8 .0 3,6 ]octanes: New Hetereocycles by Addition of Sulfonyl Azides to 7‐Substituted Norbornadienes – Experimental Verification of σ Interactions in the Norbornane Skeleton
Author(s) -
Huda Egbert,
Martin HansDieter,
Mayer Bernhard,
Somnitz KarlHeinz,
Steigel Alois,
Haddad Hatim,
Distefano Guiseppe,
Modelli Alberto
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911241232
Subject(s) - chemistry , sulfonyl , nuclear magnetic resonance spectroscopy , spectroscopy , medicinal chemistry , stereochemistry , organic chemistry , alkyl , physics , quantum mechanics
Abstract The reaction of six 7‐substituted norbornadienes with seven sulfonyl azides has been investigated. The products consist of either the novel azatetracyclic system 1 or the stereoisomeric bicycles 2 or of a mixture of them. The chemical behaviour of 1 has been studied. Mechanistically the results may be rationalized within the frame of the Mazzocchi‐Houk model. The theoretical predictions of this model, concerning the π*and σ* energies, were confirmed experimentally by using electron‐transmission spectroscopy.