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Isolation and Crystallographic Characterization of Allylindium Species Generated from Allyl Halide and Indium(0)
Author(s) -
Yasuda Makoto,
Haga Masahiko,
Baba Akio
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900955
Subject(s) - chemistry , bromide , indium , pyridine , halide , trigonal bipyramidal molecular geometry , lewis acids and bases , medicinal chemistry , reactivity (psychology) , allyl bromide , stereochemistry , crystallography , inorganic chemistry , crystal structure , organic chemistry , catalysis , medicine , alternative medicine , pathology
The reaction of cinnamyl bromide with indium(0) gave two allylindium species, cinnamylindium dibromide and dicinnamylindium bromide. Either species were isolated after complexation of appropriate pyridine‐type Lewis bases. The use of 3,5‐dibromopyridine (Br 2 py) as a Lewis base gave cinnamylindium dibromide with two Br 2 py ligands. Dicinnamylindium bromide was isolated with 4‐(dimethylamino)pyridine (Me 2 Npy) ligands. In both cases, the indium atom showed a trigonal‐bipyramidal coordination sphere with the cinnamyl group(s) and bomine atom(s) in equatorial and the pyridine‐type ligands in axial positions. The cinnamylindium bromide transformed to dicinnamylindium bromide with formation of InBr 3 in the presence of Me 2 Npy. The dicinnamylindium bromide had a higher reactivity than the monoallyl compound for carbonyl addition.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)