SYNTHETIC EXPLOITATION OF THE RING-OPENING OF 3,4-DINITROTHIOPHENE - A NOVEL ACCESS TO 1,4-DIALKYL-2,3-DINITRO-1,3-BUTADIENES AND 1,4-DIARYL-2,3-DINITRO-1,3-BUTADIENES

被引：34

作者：

DELLERBA, C

MELE, A

NOVI, M

PETRILLO, G

STAGNARO, P

机构：

[1] Istituto di Chimica Organica, C.N.R. Centro di Studio sui Diariloidi e loro Applicazioni, 16132 Genova

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(00)97773-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(E,E)-1,4-Bis(diethylamino)-2,3-dinitro-1,3-butadiene (2a), obtained from the ring-opening of 3,4-dinitrothiophene, reacts with Grignard reagents in THF to give good yields of 1,4-disubstituted ( Et, cy-Hex, Ph ) 2,3-dinitro- 1, 3-butadienes (3a-c) having almost exclusively (E,E) configuration. © 1990.

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页码：4933 / 4936

页数：4

相关论文

共 11 条

[1] REPLACEMENT OF HALOGEN BY HYDROGEN IN NITRO ARYL HALIDES - SOME APPLICATIONS IN THE THIOPHENE SERIES [J].

BLATT, AH ;

GROSS, N ;

TRISTRAM, EW .

JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (12) :1588-1590

[2] RING-OPENING REACTION IN THIOPHEN SERIES - REAACTION BETWEEN 3,4-DINITROTHIOPHEN AND SECONDARY AMINES [J].

DELLERBA, C ;

SPINELLI, D ;

LEANDRI, G .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (10) :549-&

[3]

DellErba C., 1968, B SCI FAC CHIM IND B, V26, P97

[4] SYNTHESIS AND MICROBIAL TOXICITY OF DINITROBUTADIENES AND RELATED COMPOUNDS [J].

DURDEN, JA ;

HEYWOOD, DL ;

SOUSA, AA ;

SPURR, HW .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1970, 18 (01) :50-&

[5]

ELAGIN LM, 1971, DOKL AKAD NAUK SSSR+, V201, P1356

[6]

KROWCZYNSKI A, 1986, B POL ACAD SCI-CHEM, V34, P341

[7] STEREOCHEMISTRY OF THERMAL-ISOMERIZATION OF 1,3-DINITRO-2,4-DIPHENYLCYCLOBUTENES AND 1,3-DINITRO-2,4-DIPHENYLBUTADIENES - CIS, TRANS ISOMERISM OF BETA-NITROSTYRENES [J].

MILLER, DB ;

FLANAGAN, PW ;

SHECHTER, H .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) :2112-2220

[8]

PODGORNO.NN, 1974, ZH ORG KHIM+, V10, P1985

[9] NITROENAMINES - PREPARATION, STRUCTURE AND SYNTHETIC POTENTIAL [J].

RAJAPPA, S .

TETRAHEDRON, 1981, 37 (08) :1453-1480

[10] SYNTHESIS OF ALIPHATIC DINITRODIENES [J].

ROWLEY, GL ;

FRANKEL, MB .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (05) :1512-&