Formal [1,3] rearrangement of 2-furylmethyl and 2-thienylmethyl vinyl ethers

被引：12

作者：

Palani, N

Balasubramanian, KK

机构：

[1] INDIAN INST TECHNOL,DEPT CHEM,MADRAS 600036,TAMIL NADU,INDIA

[2] SPIC SCI FDN,CTR AGROCHEM RES,MADRAS 600032,TAMIL NADU,INDIA

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 52期

关键词：

D O I：

10.1016/0040-4039(95)02038-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzyl and naphthylmethyl vinyl ethers are inert in LPDE medium, whereas heteroaromatic methyl vinyl ethers, viz., 2-furyl and 2-thienylmethyl vinyl ethers undergo formal [1,3] rearrangement in LPDE medium.

引用

页码：9527 / 9530

页数：4

共 11 条

[1]

ACHESON RM, 1967, INTRO CHEM HETEROCYC, P113

[2] SYNTHESIS OF GLYCOSIDES OF FUCOSE UNDER NEUTRAL CONDITIONS IN SOLUTIONS OF LICLO4 IN ORGANIC-SOLVENTS [J].

BOHM, G ;

WALDMANN, H .

TETRAHEDRON LETTERS, 1995, 36 (22) :3843-3846

[3]

BURGSTAHLER AW, 1963, CHEM BER, P4986

[4] [1,3] SIGMATROPIC REARRANGEMENT OF ALLYL VINYL ETHERS AT AMBIENT-TEMPERATURE IN 3.0M LITHIUM PERCHLORATE-DIETHYL ETHER [J].

GRIECO, PA ;

CLARK, JD ;

JAGOE, CT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5488-5489

[5] DIRECT SUBSTITUTION OF SECONDARY ALLYLIC ALCOHOLS WITH O-SILYLATED KETENE ACETALS IN 3.0 M LITHIUM PERCHLORATE-DIETHYL ETHER - AN ALTERNATIVE TO THE [1,3] SIGMATROPIC REARRANGEMENT OF ALLYL VINYL ETHERS [J].

GRIECO, PA ;

COLLINS, JL ;

HENRY, KJ .

TETRAHEDRON LETTERS, 1992, 33 (33) :4735-4738

[6]

KATRITZKY AR, 1985, HDB HETEROCYCLIC CHE, P277

[7]

LENOBLE WJ, 1969, CHEM IND-LONDON, P378

[8] REARRANGEMENTS OF SOME FURAN AND BENZOFURAN 1,5,-DIENOLS [J].

MARTIN, D ;

WURSTER, JA ;

BOYLAN, MJ ;

BORZILLERI, RM ;

ENGEL, GT ;

WALSH, EJ .

TETRAHEDRON LETTERS, 1993, 34 (52) :8395-8398

[9] LITHIUM PERCHLORATE DIETHYL-ETHER - INDUCED REARRANGEMENT OF EPIMERIC ENDOCYCLOPENTADIENYL AND EXOCYCLOPENTADIENYL DICYCLOPENTADIENYL VINYL ETHERS [J].

PALANI, N ;

BALASUBRAMANIAN, KK .

TETRAHEDRON LETTERS, 1993, 34 (31) :5001-5004

[10] PYROLYSIS OF FUR-2-YLMETHYL VINYL ETHERS [J].

THOMAS, AF .

HELVETICA CHIMICA ACTA, 1970, 53 (03) :605-&

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