REACTIONS OF TRIAZOLINEDIONE WITH ALKENES - A REMARKABLE GEMINAL SELECTIVITY

被引：25

作者：

ORFANOPOULOS, M

ELEMES, Y

STRATAKIS, M

机构：

[1] Department of Chemistry, University of Crete, 71110 Iraklion, Crete

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(00)97956-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ene reaction of N-Phenyl-1,2,4-triazoline-3,5-dione with alkenes shows a remarkable preference for hydrogen abstraction from the group which is geminal to the larger substituent of the double bond. These results require that the dominant effect in the transition state of the ene reaction is the nonbonded interactions. © 1990.

引用

页码：5775 / 5778

页数：4

共 20 条

[1] ADAM W, 1986, SYNTHESIS-STUTTGART, P1050
[2] HOW MECHANISTICALLY EQUIVALENT ARE SINGLET OXYGEN AND TRIAZOLINEDIONE - REGIOCHEMICAL AND STEREOCHEMICAL DIFFERENCES IN THEIR ENE REACTIONS WITH ALLYLSILANES
ADAM, W
SCHWARM, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) : 3129 - 3130
[3] ON THE MECHANISM OF THE CYCLOADDITION OF 1,2,4-TRIAZOLINE-3,5-DIONES WITH BICYCLOALKENES LEADING TO REARRANGED URAZOLES
ADAM, W
CARBALLEIRA, N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) : 2874 - 2882
[4] SINGLET OXYGEN AND TRIAZOLINEDIONE ADDITIONS TO ALPHA,BETA-UNSATURATED SULFOXIDES
AKASAKA, T
MISAWA, Y
GOTO, M
ANDO, W
[J]. TETRAHEDRON, 1989, 45 (21) : 6657 - 6666
[5] AKASAKA T, 1987, TETRAHEDRON LETT, P6633
[6] SELECTIVE HALOGENATION OF STEROIDS USING ATTACHED ARYL IODIDE TEMPLATES
BRESLOW, R
CORCORAN, RJ
SNIDER, BB
DOLL, RJ
KHANNA, PL
KALEYA, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (03) : 905 - 915
[7] REACTION OF ELECTROPHILES WITH UNSATURATED SYSTEMS - TRIAZOLINEDIONE-OLEFIN REACTIONS
CHENG, CC
SEYMOUR, CA
PETTI, MA
GREENE, FD
BLOUNT, JF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) : 2910 - 2916
[8] GEMINAL SELECTIVITY IN SINGLET OXYGEN REACTIONS
CLENNAN, EL
CHEN, XN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) : 3124 - 3125
[9] COREY EJ, 1973, TETRAHEDRON LETT, P3091
[10] REACTIONS OF TRIAZOLINEDIONES WITH CIS-ALKENES - A HIGHLY REGIOSELECTIVE ENE REACTION
ELEMES, Y
STRATAKIS, M
ORFANOPOULOS, M
[J]. TETRAHEDRON LETTERS, 1989, 30 (49) : 6903 - 6906

← 1 2 →