Four‐Center Two‐Electron Bonding in a Tetrahedral Topology. Experimental Realization of Three‐Dimensional Homoaromaticity in the 1,3‐Dehydro‐5,7‐adamantanediyl Dication | Zendy

Bremer Matthias | Zendy; von Ragué Schleyer Paul | Zendy; Schötz Karl | Zendy; Kausch Michael | Zendy; Schindler Michael | Zendy

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Four‐Center Two‐Electron Bonding in a Tetrahedral Topology. Experimental Realization of Three‐Dimensional Homoaromaticity in the 1,3‐Dehydro‐5,7‐adamantanediyl Dication

Author(s) -

Bremer Matthias,

von Ragué Schleyer Paul,

Schötz Karl,

Kausch Michael,

Schindler Michael

Publication year - 1987

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198707611

Subject(s) - dication , realization (probability) , chemistry , methylene , tetrahedron , crystallography , center (category theory) , stereochemistry , topology (electrical circuits) , computational chemistry , ion , combinatorics , mathematics , medicinal chemistry , organic chemistry , statistics

A nonclassical structure for the dication 3 is supported, in particular, by the 13 C‐NMR data: the signals of the bridgehead C atoms are shifted upfield (δ = 6.6) and not downfield, as would have been expected for a classical dication. The resonances of the methylene C atoms are observed at δ = 35.6 ( 1 H‐NMR: δ = 3.8). Compound 3 is synthesized starting from 1,3,5,7‐tetra‐iodoadamantane, which reacts with HgF 2 to give 1. Compound 1 reacts with n BuLi to give 2 , from which 3 can be generated. The dication 3 is stable up to 0°C.

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