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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.