Synthesis of new sterically hindered anilines

被引：6

作者：

Steele, Barry R. ^{[1
]}

Georgakopoulos, Spyros ^{[1
]}

Micha-Screttas, Maria ^{[1
]}

Screttas, Constantinos G. ^{[1
]}

机构：

[1] Natl Hellen Res Fdn, Inst Organ & Pharmaceut Chem, GR-11635 Athens, Greece

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 19期

关键词：

metalation; alkylation; amines; steric hindrance; carbanions; BASE-CATALYZED HYDROAMINATION; INTRAMOLECULAR HYDROAMINATION; ETHYLENE; ETHYLATION; METATHESIS; COMPLEXES; ALKENES; BEARING; LIGAND;

D O I：

10.1002/ejoc.200700233

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring-alkylated primary, secondary and tertiary anilines have been ethylated with ethylene at benzylic positions in a simple and inexpensive one-pot procedure which is mediated by the use of the superbase system nBuLi/LiK(OCH2 CH2NMe2)(2) in the presence of Mg(OCH2CH2OEt)(2), Primary and secondary anilines are ethylated readily at ortho-benzylic positions but with difficulty or not at all at other positions. Tertiary anilines are ethylated at all positions. Mono- or diethylation occurs depending on the steric constraints present.

引用

页码：3091 / 3094

页数：4

共 50 条

[21] SYNTHESIS OF STERICALLY HINDERED STILBENES OF BIOLOGICAL IMPORTANCE
JAMES, BG
PATTENDEN, G
BARLOW, L
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (13): : 1466 - 1475
[22] A SIMPLE METHOD FOR THE SYNTHESIS OF THE STERICALLY HINDERED CHLORAMINES
ZAKRZEWSKI, J
SYNTHETIC COMMUNICATIONS, 1988, 18 (16-17) : 2135 - 2140
[23] An efficient synthesis of sterically hindered arylboronic acids
Fang, H
Kaur, G
Yan, J
Wang, B
TETRAHEDRON LETTERS, 2005, 46 (10) : 1671 - 1674
[24] A CONVENIENT SYNTHESIS OF STERICALLY HINDERED GEMINAL DIBROMIDES
GUZIEC, FS
SANFILIPPO, LJ
SYNTHESIS-STUTTGART, 1988, (07): : 547 - 549
[25] Synthesis of copolymers with sterically hindered and polar monomers
Donner, M
Fernandes, M
Kaminsky, W
MACROMOLECULAR SYMPOSIA, 2006, 236 : 193 - 202
[26] Sterically hindered β-diketones: Synthesis and applications in catalysis
Crossman, Aaron
Marshak, Michael
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[27] SYNTHESIS AND SOME REACTIONS OF STERICALLY HINDERED QUINOAZIDES
RAZUVAEV, GA
ABAKUMOV, GA
KLIMOV, ES
NECHUEV, AI
DOKLADY AKADEMII NAUK SSSR, 1974, 215 (06): : 1390 - 1393
[28] Synthesis of Sterically Hindered Polychlorinated Biphenyl Derivatives
Joshi, S. N.
Vyas, S. M.
Duffel, M. W.
Parkin, S.
Lehmler, H. -J.
SYNTHESIS-STUTTGART, 2011, (07): : 1045 - 1054
[29] SYNTHESIS AND PROPERTIES OF SIMPLE AND OF STERICALLY HINDERED PHOSPHANEALKYLENEBORANES
SCHMIDBAUR, H
MULLER, G
BLASCHKE, G
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (04): : 1480 - 1486
[30] New Metal Chelates with Sterically Hindered Azo Ligands: Synthesis and Physicochemical Properties
V. A. Kogan
S. N. Lyubchenko
I. N. Shcherbakov
A. M. Ionov
V. V. Tkachev
G. V. Shilov
S. M. Aldoshin
Russian Journal of Coordination Chemistry, 2005, 31 : 533 - 540

← 1 2 3 4 5 →