FLUORINATED ACETYLENES .14. REACTION OF HEXAFLUOROBUT-2-YNE WITH 3-CARBOETHOXYFURAN AND WITH CYCLOHEPTATRIENE

被引：6

作者：

BARLOW, MG ^{[1
]}

SULIMAN, NNE ^{[1
]}

TIPPING, AE ^{[1
]}

机构：

[1] UNIV MANCHESTER,INST SCI & TECHNOL,DEPT CHEM,MANCHESTER M60 1QD,LANCS,ENGLAND

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1995年 / 70卷 / 01期

关键词：

FLUORINATED ACETYLENES; HEXAFLUOROBUT-2-YNE; 3-CARBOETHOXYFURAN; CYCLOHEPTATRIENE; NMR SPECTROSCOPY; IR SPECTROSCOPY; MASS SPECTROMETRY; DIELS-ALDER ADDUCTS;

D O I：

10.1016/0022-1139(94)03100-E

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of 3-carboethoxyfuran (4) with hexafluorobut-2-yne (5) (1:2 molar ratio) at room temperature in dichloromethane afforded the Diels-Alder 1:1 adduct (3) (7%) and three 2:1 adducts formed by further addition of the furan 4 across the least substituted double bond of 1:1 adduct 3, i.e. the exo,endo- (8a) (39.5%), exo,exo- (9a) (24%) and exo,exo- (10a) (24%) isomers in which the two CO(2)Et groups are 1,4, 1,4 and 1,3 to each other, respectively. A mixture of furan 4 and the 1:1 adduct 3, heated at 50 degrees C in dichloromethane, gave the 2:1 adducts 8a (38%), 9a (25%) and 10a (28%). A comparison reaction of furan 4 with dimethyl acetylenedicarboxylate (DMAD) (6) at 80 degrees C yielded the corresponding 2:1 adducts gb (33%), 9b (14%) and 10b (30%); reaction did not occur at room temperature. A mixture of cycloheptatriene (7) and butyne 5 heated at 80 degrees C gave only the 1:1 adduct (13) (93%) of the isomeric norcaradiene (18) and butyne 5.

引用

页码：95 / 102

页数：8

共 14 条

[1] NOVEL DIELS-ALDER CYCLOADDITION INVOLVING 2ALPHA,BETA-UNSATURATED ESTERS IN THE FORMATION OF ISOCOUMARINS FROM THE REACTION OF ETHYL PROPYNOATE WITH 3,4-BIS(TRIFLUOROMETHYL)FURAN [J].

ABUBAKAR, AB ;

BOOTH, BL ;

TIPPING, AE .

JOURNAL OF FLUORINE CHEMISTRY, 1990, 47 (02) :353-359

[2] SOME REACTIONS OF 3,4-BIS(TRIFLUOROMETHYL)FURAN AND ITS PRECURSOR, 2,3-BIS(TRIFLUOROMETHYL)-7-OXABICYCLO[2,2,1]HEPTA-2,5-DIENE - NOVEL ISOCOUMARIN FORMATION FROM THERMAL-REACTION OF THE FURAN WITH ETHYL PROPYNOATE [J].

ABUBAKAR, AB ;

BOOTH, BL ;

SULIMAN, NNE ;

TIPPING, AE .

JOURNAL OF FLUORINE CHEMISTRY, 1992, 56 (03) :359-371

[3] FLUORINATED ACETYLENES .13. SYNTHESIS OF 1,6-DIPHENYL-3,3,4,4-TETRAFLUOROHEXA-1,5-DIYNE [J].

BARLOW, MG ;

TAJAMMAL, S ;

TIPPING, AE .

JOURNAL OF FLUORINE CHEMISTRY, 1993, 64 (1-2) :61-71

[4]

BARLOW MG, IN PRESS ACTA CRYSTA

[5] THERMAL, NONCATALYTIC CYCLOADDITIONS OF ACRYL COMPOUNDS ON CYCLOHEPTATRIENE [J].

BELLUS, D ;

HELFERIC.G ;

WEIS, CD .

HELVETICA CHIMICA ACTA, 1971, 54 (02) :463-&

[6]

GOLDSTEIN MJ, 1965, TETRAHEDRON LETT, P4413

[7] RE-EXAMINATION OF CYCLOADDITION OF CYCLOHEPTATRIENE WITH MALEIC ANHYDRIDE [J].

ISHITOBI, H ;

TANIDA, H ;

TORI, K ;

TSUJI, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (11) :2993-+

[8]

LIU RSH, 1969, TETRAHEDRON LETT, P1409

[9] STEREOCHEMISTRY OF THE DIELS-ALDER REACTION [J].

MARTIN, JG ;

HILL, RK .

CHEMICAL REVIEWS, 1961, 61 (06) :537-562

[10] THE DIMER OF 2-CYANO-1,3-BUTADIENE [J].

MARVEL, CS ;

BRACE, NO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (01) :37-40

← 1 2 →