Bildung eines hochexplosiven Valenzisomeren des Indens aus Dilithiopentalen und Chlorcarben | Zendy

Burger Ulrich | Zendy; Bianco Bernard | Zendy

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Bildung eines hochexplosiven Valenzisomeren des Indens aus Dilithiopentalen und Chlorcarben

Author(s) -

Burger Ulrich,

Bianco Bernard

Publication year - 1983

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19830660107

Subject(s) - chemistry , carbene , indene , dichlorocarbene , methylene , methyllithium , medicinal chemistry , nuclear magnetic resonance spectroscopy , intramolecular force , valence (chemistry) , derivative (finance) , stereochemistry , organic chemistry , financial economics , economics , catalysis

Formation of a Highly Explosive Valence Isomer of Indene from Dilithiopentalene and Chlorocarbene The principal product of the reaction of dilithiopentalene ( 3 ) with methyllithium and methylene chloride is shown by difference‐FT‐NMR, spectroscopy to be tetracyclo[4.3.0.0 3,5 .0 4,6 ]nona‐1,7‐diene ( 8 ). This laterally bridged benzvalene derivative explodes violently at temperatures as low as −40° when concentrated. Controlled rearrangement in diluted solution gives indene ( 4 ). The key step in the formation of the tetracyclic C 9 H 8 ‐compound 8 is suggested to be an intramolecular 1,4‐carbene addition.

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