Abstract
Synthesis and characterization of soluble analogues of iodosylbenzene PhIO and (tosyliminoiodo)benzene PhINTs are reported. The syntheses of 4-trifluoromethyl-2-(tertbutylsulfonyl)iodosylbenzene (3) and 4-trifluoromethyl-2-(tert-butylsulfonyl)(tosylimino)iodobenzene (4) increase the repertoire of available soluble organoiodine(III) based oxo- and nitrene precursors. We also report the synthesis of a new organoiodine(V) compound, 4-trifluoromethyl-2-(tert-butylsulfonyl)iodylbenzene.
Highlights
Polyvalent organoiodine compounds have found wide synthetic applications in many organic transformations.[1]
Recent efforts in our group have been focussed on the solubilization of these important compounds by the modification of secondary bonding interactions.[4]
Analogues of PhIO and PhINTs were realized in the synthesis of iodosylarene 1 andarene 2, by placing an appropriate substituent in the ortho position of the phenyl ring.[6]
Summary
Polyvalent organoiodine compounds have found wide synthetic applications in many organic transformations.[1]. With the aim of further stabilization of soluble organoiodine(III) species, iodosylarene 3 and (tosyliminoiodo)arene 4, possessing the electron withdrawing trifluoromethyl group were prepared and characterized. The unsymmetrically substituted thioether 5 was synthesized from commercially available 3-(trifluoromethyl)bromobenzene by metal-halogen exchange using tBuLi followed by reaction of t-butyl disulfide Compound 5 was readily oxidized to sulfone 6 in good yield.[11] The Snieckus method for directed ortho-lithiation of sulfones was adapted for the synthesis of iodoarene 7.12 Two geometric isomers of this iodoarene (7a and 7b in a 4:1 ratio) were obtained, and the desired 7a was isolated by recrystallization of the mixture of isomers from diethyl ether.
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