The Chemistry of Alkylsulfenyl Alkylsulfinyl Thioanhydrides. The Mechanism of Decomposition
The decomposition mechanism of alkylsulfenyl alkylsulfinyl thioanhydrides has been investigated.Although the product mixture is complex in most cases, a detailed decomposition study as well as a careful analysis of the products allows for a proposal for a general mechanism which is interesting and not simple.We find, however, that the decomposition process is consistent with that of related systems.
Derbesy, Gerard,Harpp, David N.
p. 4468 - 4474
(2007/10/02)
LIGAND EXCHANGE AND LIGAND COUPLING VIA THE ?-SULFURANE INTERMEDIATE IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENTS: CONVENIENT PREPARATION OF 2,2'-BIPYRIDINES
The reaction between methyl 2-pyridyl sulfoxide (1) with Grignard reagents afforded 2,2'-bipyridine (2) in moderate yield.The reaction is considered to involve initial ligand exchange to generate 2-pyridylmagnesium halide which in the subsequent step attacks the original sulfoxide to form the ?-sulfurane that undergoes ligand coupling to afford 2.The reaction of t-butyl-2-pyridyl sulfoxide (3) with C6H5MgBr, however, gave only 2-phenylpyridine (4).This may due to steric hindrance to the initial ligand exchange.Formation of 2 is a convenient process for preparation of 2,2'-bipyridines bearing various substituents.
Oae, Shigeru,Kawai, Tsutomu,Furukawa, Naomichi
p. 123 - 132
(2007/10/02)
LIGAND COUPLING THROUGH HYPERVALENT INTERMEDIATES. REACTION OF HETEROARYL SULFOXIDES WITH ORGANOMETALLICS REAGENTS AND THEIR IMPLICATIONS.
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OAE, S.
p. 13 - 30
(2007/10/02)
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