Periselectivity in the cycloaddition reactions of pentafulvenes with 3-oxidopyrylium betaines: Effect of substituent on the C-6 carbon

被引：6

作者：

Krishnan, K. Syam ^{[1
]}

Rajan, Rani ^{[1
]}

Radhakrishnan, K. V. ^{[1
]}

机构：

[1] CSIR, Natl Inst Interdisciplinary Sci & Technol, Chem Sci & Technol Div, Organ Chem Sect, Trivandrum 695019, Kerala, India

来源：

SYNTHESIS-STUTTGART | 2008年 / 12期

关键词：

pentafulvenes; oxidopyrylium betaines; cycloaddition; periselectivity;

D O I：

10.1055/s-2008-1067093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Periselectvity in cycloaddition reactions of pentafulvenes with 3-oxidopyrylium betaines is examined. The results of our studies show that depending on the substituent on the C-6 carbon, the reaction may proceed either through the [6+3] or the [3+2] pathway. The results of our investigations with various pentafulvenes are discussed.

引用

页码：1955 / 1959

页数：5

共 50 条

[41] Molecular orbital calculations of the substituent effect on intermolecular CH/π interaction in C2H3X-C6H6 complexes (X = H, F, Cl, Br, and OH)
Takahashi, O
Kohno, Y
Saito, K
[J]. CHEMICAL PHYSICS LETTERS, 2003, 378 (5-6) : 509 - 515
[42] Substituent effects on associative reactions of the clusters Ru5C(CO)(14)L (L=P(OPh)(3) and P(C6Hl1)(3)) with phosphorus-donor nucleophiles
Farrar, DH
Hao, JB
Mourad, O
Poe, AJ
[J]. ORGANOMETALLICS, 1997, 16 (23) : 5015 - 5022
[43] PHOTOCHEMICAL CYCLOADDITION OF BENZOPHENONE WITH 1,5-DIMETHYL-6-METHYLENETRICYCLO[3.2.1.02,7]OCT-3-EN-8-ONE AND A RELATED ALCOHOL - STRIKING SUBSTITUENT EFFECT ON PRODUCT COMPOSITION
NITTA, M
SUGIYAMA, H
SEKINE, Y
[J]. CHEMISTRY LETTERS, 1977, (01) : 55 - 58
[44] NITRENE INSERTION REACTIONS .3. STERIC EFFECT OF ISOPROPYL AND TERT BUTYL GROUPS - 1,6 TYPE CYCLOADDITION OF TETRACYANOETHYLENE TO 1H-AZEPINES
PHOTIS, JM
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (05) : 729 - &
[45] Ni-Catalyzed Reductive and Merged Photocatalytic Cross-Coupling Reactions toward sp3/sp2-Functionalized Isoquinolones: Creating Diversity at C-6 and C-7 to Address Bioactive Analogues
Dumas, Adrien
Garsi, Jean-Baptiste
Poissonnet, Guillaume
Hanessian, Stephen
[J]. ACS OMEGA, 2020, 5 (42): : 27591 - 27606
[46] PHOTOIONIZATION OF PROPYLENE, CYCLOPROPANE, AND ETHYLENE - EFFECT OF INTERNAL ENERGY ON BIMOLECULAR REACTIONS OF C2H+4 AND C3H+6
SIECK, LW
AUSLOOS, P
[J]. JOURNAL OF RESEARCH OF THE NATIONAL BUREAU OF STANDARDS SECTION A-PHYSICS AND CHEMISTRY, 1972, A-76 (03): : 253 - +
[47] TOXICOLOGICAL STUDY ON EFFECT OF DIFLUBENZURON (1-(4-CHLOROPHENYL)-3-(2,6-DIFLUOROBENZOYL)-UREA) ON RAT C-6 ASTROCYTOMA-CELLS INVITRO
STOOLMILLER, AC
[J]. GENERAL PHARMACOLOGY-THE VASCULAR SYSTEM, 1978, 9 (01): : 11 - 16
[48] The substituent effect upon the iminophosphorane X3PNH for X = F, Cl, Br, H, CH3, C6H5, CH3CH2, and (CH3)3C
Lu, WC
Sun, CC
[J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2002, 593 : 1 - 7
[49] CARBIDE REACTIONS (M3C-]M7C3-]M23C6-]M6C) DURING TEMPERING OF RAPIDLY SOLIDIFIED HIGH-CARBON CR-W AND CR-MO STEELS
INOUE, A
MASUMOTO, T
[J]. METALLURGICAL TRANSACTIONS A-PHYSICAL METALLURGY AND MATERIALS SCIENCE, 1980, 11 (05): : 739 - 747
[50] ALKYL SUBSTITUENT EFFECTS IN LIGAND-INDUCED CARBON-MONOXIDE INSERTION REACTIONS IN [(ETA5-C5H5)(CO)3MO(BENZYL)] SYSTEMS
COTTON, JD
CRISP, GT
DALY, VA
[J]. INORGANICA CHIMICA ACTA-ARTICLES, 1981, 47 (02): : 165 - 169

← 1 2 3 4 5 →