CYCLIC ARYLENEAZACHALCOGENENES .8. REGIOSELECTIVITY OF FLUORIDE ION-INDUCED INTRAMOLECULAR NUCLEOPHILIC CYCLIZATION OF HEPTAFLUORONAPHTHYL SULFUR DIIMIDES 2-NF(F)-N=S=N-SIME(3) AND 2-NF(F)S-N=S=N-S1ME(3)

Authors
BAGRYANSKAYA IY GATILOV YV MILLER AO SHAKIROV MM ZIBAREV AV
Citation
Iy. Bagryanskaya et al., CYCLIC ARYLENEAZACHALCOGENENES .8. REGIOSELECTIVITY OF FLUORIDE ION-INDUCED INTRAMOLECULAR NUCLEOPHILIC CYCLIZATION OF HEPTAFLUORONAPHTHYL SULFUR DIIMIDES 2-NF(F)-N=S=N-SIME(3) AND 2-NF(F)S-N=S=N-S1ME(3), Heteroatom chemistry, 5(5-6), 1994, pp. 561-565
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Heteroatom chemistry → ACNP
ISSN journal
10427163
Volume
5
Issue
5-6
Year of publication
1994
Pages
561 - 565
Database
ISI
SICI code
1042-7163(1994)5:5-6<561:CA.ROF>2.0.ZU;2-D
Abstract
The title reaction is highly regioselective, leading in both cases to ,7,8,9-hexafluoronaphtho[1,2-c]-[1,2,5]thiadiazole (whose structure is confirmed by X-ray structure analysis) and 6,7,8,9-hexafluoronaphtho[ 2,3-c][1,2,5]thiadiazole in similar to 94:6 ratio. The preferred direc tion 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).