Solvolysis of 2-adamantyl p-toluenesulfonate in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate

被引：3

作者：

Okazaki, Takao ^{[1
]}

Ito, Koji ^{[1
]}

Kitagawa, Toshikazu ^{[1
]}

机构：

[1] Mie Univ, Grad Sch Engn, Dept Chem Mat, Tsu, Mie 5148507, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 44期

关键词：

Ionic liquids; Solvent ionizing power; Solvolysis; 2-Adamantyl; Kinetics; Grunwald-Winstein relationship; SOLVENT PROPERTIES; POLARITY; DEDIAZONIATION; HALIDES;

D O I：

10.1016/j.tetlet.2015.09.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The solvolytic rate constants of 2-adamantyl p-toluenesulfonate were determined in [BMIM][BF4] in the presence/absence of 2,6-lutidine by NMR measurements. The activation parameters suggest that the reaction proceeded by k(c) mechanism. The solvolysis quantitatively gave 2-adamantanol as a product by the reaction with the water present in the ionic liquid. The solvent ionizing power of [BMIM][BF4] was found to be similar to that of ethanol. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6066 / 6068

页数：3

共 36 条

[1]

[Anonymous], 2008, IONIC LIQUIDS SYNTHE

[2]

Anslyn E. V., 2006, MODERN PHYS ORGANIC

[3] STUDIES ON SULFATE ESTERS .I. NUCLEOPHILIC REACTIONS OF AMINES WITH P-NITROPHENYL SULFATE [J].

BENKOVIC, SJ ;

BENKOVIC, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (23) :5504-&

[4]

Bentley T.W., 1990, Prog. Phys. Org. Chem, V17, P121, DOI DOI 10.1002/9780470171967.CH5

[5] SOLVENT IONIZING POWER - COMPARISONS OF SOLVOLYSES OF 1-ADAMANTYL CHLORIDES, BROMIDES, IODIDES, AND TOSYLATES IN PROTIC SOLVENTS [J].

BENTLEY, TW ;

CARTER, GE ;

ROBERTS, K .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5183-5189

[6] Nucleophilic displacement reactions in ionic liquids:: Substrate and solvent effect in the reaction of NaN3 and KCN with alkyl halides and tosylates [J].

Chiappe, C ;

Pieraccini, D ;

Saullo, P .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6710-6715

[7] Ionic liquids: solvent properties and organic reactivity [J].

Chiappe, C ;

Pieraccini, D .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (04) :275-297

[8]

Chiappe C., 2008, IONIC LIQUIDS SYNTHE

[9] Influence of Structural Variations in Cationic and Anionic Moieties on the Polarity of Ionic Liquids [J].

Chiappe, Cinzia ;

Pomelli, Christian Silvio ;

Rajamani, Sunita .

JOURNAL OF PHYSICAL CHEMISTRY B, 2011, 115 (31) :9653-9661

[10] Carbocation-forming reactions in ionic liquids [J].

Creary, X ;

Willis, ED ;

Gagnon, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18114-18120

← 1 2 3 4 →