Synthesis and Properties of a Bridged  syn ‐Tricyclo[4.2.0.0 2,5 ]octa‐3,7‐diene: Formation of Propella[3 4 ]prismane | Zendy

Gleiter Rolf | Zendy; Karcher Michael | Zendy

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Synthesis and Properties of a Bridged syn ‐Tricyclo[4.2.0.0 2,5 ]octa‐3,7‐diene: Formation of Propella[3 4 ]prismane

Author(s) -

Gleiter Rolf,

Karcher Michael

Publication year - 1988

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.198808401

Subject(s) - cubane , diene , reactivity (psychology) , chemistry , derivative (finance) , stereochemistry , crystallography , crystal structure , organic chemistry , medicine , natural rubber , alternative medicine , pathology , financial economics , economics

How bridging can markedly change the reactivity of a compound is demonstrated by the tricyclo[4.2.0.0 2.5 ]octadiene derivative 1 . Its thermal and photochemical behavior is completely different from that of the parent compound. Upon warming, 1 undergoes a degenerate Cope rearrangement and, upon irradiation, the fourfold‐bridged cubane 2 (“propella[3 4 ]prismane”) and its isomer 3 are formed.

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