Organic Reactions at High Pressure: Cycloaddition Reactions of 11‐Methylene‐1,6‐methano[10]annulene | Zendy

Klärner FrankGerrit | Zendy; Dogan Barbara M. J. | Zendy; Weider Richard | Zendy; Ginsburg David | Zendy; Vogel Emanuel | Zendy

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Organic Reactions at High Pressure: Cycloaddition Reactions of 11‐Methylene‐1,6‐methano[10]annulene

Author(s) -

Klärner FrankGerrit,

Dogan Barbara M. J.,

Weider Richard,

Ginsburg David,

Vogel Emanuel

Publication year - 1986

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.198603461

Subject(s) - annulene , cycloaddition , methylene , adduct , tautomer , chemistry , valence (chemistry) , high pressure , medicinal chemistry , computational chemistry , photochemistry , organic chemistry , thermodynamics , catalysis , physics

A remarkable pressure dependence is exhibited by the reaction of 11‐methylene‐1,6‐methano[10]annulene with dicyanoacetylene. At normal pressure, one obtains the 1:1 adduct 1a/1b , a fluxional system that is the first example of its kind of a methylenenorcaradiene/heptafulvene valence tautomerism. At 7000 bar, the main product formed is the 2:1 adduct 2 . Despite the less favorable geometry, 2 must have been formed by [8+2] cycloaddition of dicyanoacetylene to 1b.

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