Concepedia

Regioselectivity of fluoride ion‐induced intramolecular nucleophilic cyclization of heptafluoronaphthyl sulfur diimides 2Nf<sub>F</sub>NSNSiMe<sub>3</sub> and 2Nf<sub>F</sub>SNSNS1Me<sub>3</sub>

Irina Yu. Bagryanskaya, Yu. V. Gatilov, Alexey O. Miller, Andrey V. Zibarev

Heteroatom Chemistry · 1994 · 31 citations · 9 references

DOI

Concepts

Abstract

Abstract The title reaction is highly regioselective, leading in both cases to 4,5,6,7,8,9‐hexafluoronaphtho[1,2‐c]‐[1,2,5]thiadiazole (whose struture is confirmed by X‐ray structure analysis) and 4,5,6,7,8,9‐hexafluoronaphtho[2,3‐c][1,2,5]thiadiazole in ∼94 : 6 ratio. The preferred direction of cyclization is consistent with final product thermodynamics as well as factors of kinetic control for orbital‐controlled reactions (calculated by use of frontier MOs theory).

References

9

Frontier Orbitals and Organic Chemical Reactions

Journal of Molecular Structure · 1979 · 3.4K citations

, , +13

Chemical shifts for compounds of the group IV elements silicon and tin

Brian K. Hunter, L. W. Reeves · Canadian Journal of Chemistry · 1968 · 222 citations

, , +11

Cyclic aryleneazachalcogenenes. Part III [1] synthesis of polyfluorinated 2,1,3-benzothia-(selena) diazoles

Andrey V. Zibarev, Alexey O. Miller · Journal of Fluorine Chemistry · 1990 · 49 citations

, , +3

Toward molecular wire: Synthesis, crystal, molecular, and π‐electronic structure of 1,7‐bis(aryl)‐1,3,5,7‐tetraaza‐2,4,6‐trithia‐1,2,5,6‐heptatetraenes

Andrey V. Zibarev, Alexey O. Miller, Yu. V. Gatilov et al. · Heteroatom Chemistry · 1990 · 41 citations

, , +11

Cyclic aryleneazachalcogenenes—VI. Synthesis, crystal and molecular structure of 5,6,7,8-tetrafluoro-1,3,2,4-benzodithiadiazine, a formally antiaromatic stable compound

Andrey V. Zibarev, Yu. V. Gatilov, Alexey O. Miller · Polyhedron · 1992 · 37 citations

, , +11