Ligand coupling mechanism of nucleophilic vinylic substitution of iodonium salts with hypervalent 10-I-3 and 12-I-4 intermediates

被引：28

作者：

Okuyama, T ^{[1
]}

Takino, T ^{[1
]}

Sato, K ^{[1
]}

Ochiai, M ^{[1
]}

机构：

[1] UNIV TOKUSHIMA, FAC PHARMACEUT SCI, TOKUSHIMA 770, JAPAN

来源：

CHEMISTRY LETTERS | 1997年 / 09期

关键词：

D O I：

10.1246/cl.1997.955

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of 2-bromo-1-decenyl iodonium salt with bromide ion in acetonitrile results in nucleophilic substitution with complete retention. Observed rate constants show unexpected dependence on the bromide concentration, conforming with a mechanism involving ligand coupling within a bromoiodane 10-I-3 intermediate.

引用

页码：955 / 956

页数：2

共 9 条

[1] Ligand Coupling Mechanism of Nucleophilic Vinylic Substitution of Iodonium Salts with Hypervalent 10-I-3 and 12-I-4 Intermediates
Okuyama, T.
Takino, T.
Sato, K.
Ochiai, M.
Chemistry Letters, (09):
[2] DIRECTED DILITHIATION OF HEXAFLUOROCUMYL ALCOHOL - FORMATION OF A REAGENT FOR THE FACILE INTRODUCTION OF A STABILIZING BIDENTATE LIGAND IN COMPOUNDS OF HYPERVALENT SULFUR (10-S-4), PHOSPHORUS (10-P-5), SILICON (10-SI-5), AND IODINE (10-I-3)
PEROZZI, EF
MICHALAK, RS
FIGULY, GD
STEVENSON, WH
DESS, DB
ROSS, MR
MARTIN, JC
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06): : 1049 - 1053
[3] INTRAMOLECULAR ACTIVATION OF METAL-CARBONYL CLUSTER COMPLEXES - KINETICS AND MECHANISM OF LIGAND SUBSTITUTION-REACTIONS OF [OS3(CO)10LX]-(L=PPH3, CO X=CL, BR, I, NCO)
SHEN, JK
BASOLO, F
ORGANOMETALLICS, 1993, 12 (08) : 2942 - 2946
[4] Tris(trifluoromethyl)tellurate(II), [Te(CF3)3]-, the dimeric bis(trifluoromethyl)chlorotellurate(II), [(CF3)2TeCl]22-, and bis(trifluoromethyl)iodate(l), [I(CF3)2]-:: the first hypervalent alkyl [10-Te-3] and [12-Te-4] species and a novel [10-I-2] compound
Kirij, NV
Yagupolskii, YL
Maggiarosa, N
Tyrra, W
Naumann, D
JOURNAL OF FLUORINE CHEMISTRY, 2001, 112 (02) : 213 - 218
[5] Synthesis, structures, and conductivities of salts (BEDT-TTF)[9,9′(12′)-I2-3,3′-Co(1,2-C2B9H10)2] and (TTF)[9,9′,12,12′-I4-3,3′-Co(1,2-C2B9H9)2]
O. N. Kazheva
G. G. Aleksandrov
A. V. Kravchenko
V. A. Starodub
G. G. Zhigareva
I. B. Sivaev
V. I. Bregadze
L. I. Buravov
L. V. Titov
O. A. D’yachenko
Russian Chemical Bulletin, 2010, 59 : 1137 - 1144
[6] Synthesis, structures, and conductivities of salts (BEDT-TTF)[9,9′(12′)-I2-3,3′-Co(1,2-C2B9H10)2] and (TTF)[9,9′,12,12′-I4-3,3′-Co(1,2-C2B9H9)2]
Kazheva, O. N.
Aleksandrov, G. G.
Kravchenko, A. V.
Starodub, V. A.
Zhigareva, G. G.
Sivaev, I. B.
Bregadze, V. I.
Buravov, L. I.
Titov, L. V.
D'yachenko, O. A.
RUSSIAN CHEMICAL BULLETIN, 2010, 59 (06) : 1137 - 1144
[7] Ligand substitution reactions at the nickel of [Mo3NiS4(H2O)(10)](4+) with two water soluble phosphines, CO, Br-, I-, and NCS- and the inertness of the 1,4,7-triazacyclononane (L) complex [Mo-3(NiL)S-4(H2O)(9)](4+)
Saysell, DM
Borman, CD
Kwak, CH
Sykes, AG
INORGANIC CHEMISTRY, 1996, 35 (01) : 173 - 178
[8] Ligand Substitution Reactions at the Nickel of [Mo3NiS4(H2O)10]4+ with Two Water Soluble Phosphines, CO, Br-, I-, and NCS- and the Inertness of the 1,4,7-Triazacyclononane (L) Complex [Mo3(NiL)S4(H2O)9]4+
Inorg Chem, 1 (173):
[9] PREPARATION AND SPECTROSCOPIC PROPERTIES OF COBALT(III), NICKEL(II), COPPER(II) AND ZINC(II) COMPLEXES WITH A NOVEL SATURATED MACROCYCLIC LIGAND - 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22-DOCOSAHYDRODIBENZO-[B,I][1,4,8,11] TETRAAZACYCLOTETRADECINE
SAKATA, K
WADA, S
SATO, N
KURISU, M
HASHIMOTO, M
KATO, Y
INORGANICA CHIMICA ACTA, 1986, 119 (02) : 111 - 119

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