V. V. Zhdankin, Ch. J. Kuehl, A. M. Arif, P. J. Stang, “Synthesis and X-ray crystal structure of l-cyano-3,3-bis(trifluoromethyl)-l,3-dihydro-lλ<sup>3</sup>,2-benzoiodoxole, a stable cyanoiodolane”, Mendeleev Commun., 1996, Volume 6, Issue 2,Pages <nobr>50

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Synthesis and X-ray crystal structure of l-cyano-3,3-bis(trifluoromethyl)-l,3-dihydro-lλ³,2-benzoiodoxole, a stable cyanoiodolane

V. V. Zhdankin^a, Ch. J. Kuehl^a, A. M. Arif^b, P. J. Stang^b

^a Department of Chemistry, University of Minnesota Duluth, Duluth, Minnesota, USA
^b Department of Chemistry, University of Utah, Salt Lake City, Utah, USA

Abstract: Stable, crystalline cyanoiodolane 3 has been prepared in two steps by sequential reactions of l-hydroxy-3,3-bis(trifluoromethyl)-l,3-dihydro-lλ³,2-benzoiodoxole 1 with trimethylsilyltriflate and then with cyanotrimethysilane; X-ray structure analysis reveals a distorted T-shaped structure for iodine with an endocyclic I-O bond distance of 2.117 A, which is significantly shorter than usual in C-substituted benzoiodoxole derivatives.

Language: English

DOI: 10.1070/MC1996v006n02ABEH000575