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 | Zendy

Huda Egbert | Zendy; Martin HansDieter | Zendy; Mayer Bernhard | Zendy; Somnitz KarlHeinz | Zendy; Steigel Alois | Zendy; Haddad Hatim | Zendy; Distefano Guiseppe | Zendy; Modelli Alberto | Zendy

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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

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.

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