BASE-CATALYSED REARRANGEMENT OF THEBAINEHYDROQUINONES

被引：2

作者：

BARNEIS, ZJ

CARR, JD

WARNET, RJ

WHEELER, DMS

机构：

[1] Department of Chemistry, University of Nebraska, Lincoln

来源：

TETRAHEDRON | 1968年 / 24卷 / 14期

关键词：

D O I：

10.1016/S0040-4020(01)88415-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On the basis of spectra and pKa values structures are assigned to the monomethyl ethers of thebainehydroquinone. Thebeinehydroquinone (1a) and its 21-methyl ether (1b) rearrange under basic conditions to the corresponding flavothebaones (2a and 2c). The 18-methyl ether (1c) does not rearrange. A mechanism involving a cyclopropane intermediate is proposed for the rearrangements. © 1968.

引用

收藏

页码：5053 / &

相关论文

共 11 条

[1] NEIGHBORING CARBON AND HYDROGEN .51. DIENONES FROM ARO-3 PARTICIPATION - ISOLATION AND BEHAVIOR OF SPIRO(2,5)OCTA-1,4-DIENE-3-ONE [J].

BAIRD, R ;

WINSTEIN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (05) :567-&

[2]

BARNEIS ZJ, 1965, TETRAHEDRON LETT, P275

[3]

BENTLEY KW, 1956, CHEM IND-LONDON, P1353

[4] FLAVOTHEBAONE .1. PRELIMINARY WORK - SPECTRAL STUDIES AND ACETOLYSIS [J].

BENTLEY, KW ;

DOMINGUEZ, J .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (12) :1348-1352

[5] NOVEL ANALGESICS AND MOLECULAR REARRANGEMENTS IN MORPHINE-THEBAINE GROUP .6. BASE-CATALYZED REARRANGEMENTS IN 6,14-ENDO-ETHENOTETRAHYDROTHEBAINE SERIES [J].

BENTLEY, KW ;

HARDY, DG ;

CROCKER, HP ;

HADDLESEY, DI ;

MAYOR, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3312-+

[6] FLAVOTHEBAONE .3. STRUCTURE OF FLAVOTHEBAONE [J].

BENTLEY, KW ;

DOMINGUEZ, J ;

RINGE, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (04) :418-422

[7] STRUCTURE OF PRODUCTS OF PHOTOCHEMICAL REARRANGEMENT OF ADDUCT OF THEBAINE WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].

KANEMATSU, K ;

SASAKI, T .

CHEMICAL COMMUNICATIONS, 1967, (19) :988-+

[8] THE STRUCTURE OF FLAVOTHEBAONE [J].

MEINWALD, J ;

WILEY, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (10) :2569-2573

[9]

MEINWALD J, 1956, CHEM IND-LONDON, P957

[10] THE SYNTHESIS AND REARRANGEMENT OF SOME BENZONORBORNENES [J].

MEINWALD, J ;

WILEY, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3667-3671