CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS

被引：3

作者：

HOFFMANN, R

MATTAY, J

BANNING, A

RODEWALD, U

MOLLER, MM

机构：

[1] UNIV MUNSTER,INST ORGAN CHEM,ORLEANSRING 23,D-48149 MUNSTER,GERMANY

[2] UNIV MUNSTER,INST ANORGAN CHEM,D-48149 MUNSTER,GERMANY

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1994年 / 336卷 / 04期

关键词：

D O I：

10.1002/prac.19943360413

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The thermal extrusion of SO2 from disubstituted 3-sulfolenes 3 leads to 2,3-donor-acceptor-substituted 1,3-butadienes 4. These dienes react with acrylic acid ester and ethyl vinyl ether to the corresponding Diels-Alder adducts 5 and 6 and with themselves to the cyclic dimerization products 7 and 8. The regiochemistry of the cycloadducts has been determined by chemical- and NMR-methods. The pyrolysis of 3-sulfolene 11 afforded the thiolactone 13 whose structure has been verified by X-ray diffraction analysis. In addition, the influence of Lewis acid catalysts on the Diels-Alder reaction and an approach to transition state calculation by means of the semiempirical AM 1 method has also been investigated.

引用

页码：343 / 349

页数：7

共 18 条

[1] PREPARATION AND DIELS-ALDER REACTIVITY OF SEVERAL NEW CHALCOGEN-HALOGEN SUBSTITUTED BUTADIENES
BRIDGES, AJ
FISCHER, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) : 2954 - 2961
[2] BIOTIN .2. 3,4-TRANS-DIAMINOTHIOPHANE
BROWN, GB
BAKER, BR
BERNSTEIN, S
SAFIR, SR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1947, 12 (01) : 155 - 159
[3] 2-ACETYL-3-(PHENYLTHIO)-1,3-BUTADIENE - A NOVEL DIELS-ALDER DIENE AND DIENOPHILE
CHOU, SSP
TSAI, CY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22) : 5305 - 5308
[4] COMPETITION FOR REGIOCHEMICAL CONTROL BETWEEN SUBSTITUENTS OF SOME 2,3-DISUBSTITUTED BUTA-1,3-DIENES IN THE DIELS-ALDER REACTIONS
CHOU, TS
CHANG, CY
WU, MC
HUNG, SH
LIU, HM
YEH, WY
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (22) : 1643 - 1644
[5] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL
DEWAR, MJS
ZOEBISCH, EG
HEALY, EF
STEWART, JJP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) : 3902 - 3909
[6] DEWAR MJS, QCPE455
[7] FLEMING I, 1975, FRONTIER ORBITALS OR
[8] HOFFMANN R, 1990, THESIS MUNSTER
[9] KOBBING S, UNPUB CHEM BER
[10] Experiments on the synthesis of the terpenes Part X Synthesis of carvestrene and its derivatives
Perkin, WH
Tattersall, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1907, 91 : 480 - 504

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