The reaction between bis(trialkyltin) chalcogenides
and trimethylaluminum results in the
formation of bis(dimethylaluminum) chalcogenides,
(Me2Al)2E, where E is S, Se, or
Te.
Reaction between the latter and carbonyl groups (but not
carboxylic acids or esters) converts
them to carbon−chalcogen double-bond (CE) compounds. Using
this procedure, we have
successfully synthesized several telluro- and selenocarbonyl compounds.
The first successful
synthesis of an isolable, crystalline telluroformamide,
4-(telluroformyl)morpholine (3c,
C5H9NOTe), and its crystal structure are reported. Also, the syntheses
and crystal structures of
a γ-tellurolactam, 1-methyl-2-telluroxopyrroline (3d,
C5H9NTe), and two selenoamides,
N,N-diphenylselenoformamide (3a,
C13H11NSe) and
N-methyl-N-(4-nitrophenyl)
selenoformamide
(3b,
C8H8N2O2Se) are
described.
The Arbuzov reaction of (2S,4S)-4-methyl-2-phenyl-1,3,2-dioxaphosphorinane with various alkyl halides gave the diastereomerically pure phosphinates with regioselective cleavage of the primary carbon–oxygen bond. These phosphinates reacted with Grignard reagents to give optically active phosphine oxides in high optical yields.
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