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)

被引：28

作者：

BAGRYANSKAYA, IY ^{[1
]}

GATILOV, YV ^{[1
]}

MILLER, AO ^{[1
]}

SHAKIROV, MM ^{[1
]}

ZIBAREV, AV ^{[1
]}

机构：

[1] RUSSIAN ACAD SCI,INST ORGAN CHEM,NOVOSIBIRSK 630090,RUSSIA

来源：

HETEROATOM CHEMISTRY | 1994年 / 5卷 / 5-6期

关键词：

D O I：

10.1002/hc.520050523

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 structure is confirmed by X-ray structure analysis) and 4,5,6,7,8,9-hexafluoronaphtho[2,3-c][1,2,5]thiadiazole in similar to 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).

引用

页码：561 / 565

页数：5

共 15 条

[1]

ABEZGAUZ FI, 1965, ZH VSES KHIM OVA+, V10, P113

[2]

BLIZNYUK AA, 1986, ZH STRUKT KHIM, V27, P190

[3] PARTIALLY FLUORINATED HETEROCYCLIC-COMPOUNDS .28. THE HYDROLYSIS OF 1,3,4,5,6,7,8-HEPTAFLUORO-2-NAPHTHYLIDENERHODANINE TO FORM RING-FUSED THIOPHENES - A SIGNIFICANT PROPORTION OF A LINEAR NAPHTHO[2,3-B]THIOPHENE DERIVATIVE ACCOMPANYING AN ANGULAR NAPHTHO[1,2-B]THIOPHENE DERIVATIVE [J].

BROOKE, GM ;

MEARA, JM .

JOURNAL OF FLUORINE CHEMISTRY, 1990, 50 (02) :229-242

[4] PARTIALLY FLUORINATED HETEROCYCLIC-COMPOUNDS .26. AN INVESTIGATION INTO THE MODE OF CYCLIZATION IN THE REACTION OF LITHIUM 1,3,4,5,6,7,8-HEPTAFLUORO-2-NAPHTHALENETHIOLATE WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].

BROOKE, GM .

JOURNAL OF FLUORINE CHEMISTRY, 1989, 43 (03) :393-403

[5]

FLEMING I, 1977, FRONTIER ORBITALS OR

[6]

HANTER BK, 1968, CAN J CHEM, V46, P1399

[7] HE-I PHOTOELECTRON-SPECTRA AND PI-ELECTRONIC STRUCTURE OF 1,3,2,4-BENZODITHIADIAZINE AND 5,6,7,8-TETRAFLUORO-1,3,2,4-BENZODITHIADIAZINE, FORMALLY ANTIAROMATIC 12-PI-ELECTRON COMPOUNDS [J].

PETRACHENKO, NE ;

GATILOV, YV ;

ZIBAREV, AV .

JOURNAL OF ELECTRON SPECTROSCOPY AND RELATED PHENOMENA, 1994, 67 (03) :489-492

[8]

Ponomarev V. I., 1976, Soviet Physics - Crystallography, V21, P215

[9] POLYHALOGENOAROMATIC COMPOUNDS .6. NUCLEOPHILIC REACTIONS OF POLYFLUORONAPHTHALENES, NN-DISUBSTITUTED AMINOPOLYFLUORONAPHTHALENE N-OXIDES, AND NN-DISUBSTITUTED AMINOPENTAFLUOROBENZENE N-OXIDES [J].

PRICE, D ;

SUSCHITZKY, H ;

HOLLIES, JI .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (15) :1967-+

[10]

SCHERER OJ, 1970, Z NATURFORSCH PT B, VB 25, P1486

← 1 2 →