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

[11] Synthesis of a sterically hindered metallocene catalyst
Clifford, Kaitlin M.
Broene, Richard D.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[12] Synthesis of sterically hindered benzoquinone methacrylates
M. P. Shurygina
O. V. Markina
N. O. Druzhkov
T. I. Kulikova
A. V. Cherkasov
A. V. Piskunov
S. A. Chesnokov
V. K. Cherkasov
Russian Chemical Bulletin, 2012, 61 : 1215 - 1219
[13] Synthesis of sterically hindered cyclic amines
Santhan-Oommen, Reuben
Daugulis, Olafs
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[14] Synthesis of sterically hindered benzoquinone methacrylates
Shurygina, M. P.
Markina, O. V.
Druzhkov, N. O.
Kulikova, T. I.
Cherkasov, A. V.
Piskunov, A. V.
Chesnokov, S. A.
Cherkasov, V. K.
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (06) : 1215 - 1219
[15] SYNTHESIS OF STERICALLY HINDERED AROMATIC DIALDEHYDES
YAKUBOV, AP
TSYGANOV, DV
BELENKII, LI
KRAYUSHKIN, MM
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1991, 40 (07): : 1509 - 1512
[16] Synthesis of sterically hindered phosphonamidothiolates and phosphonamidodithioates
Rodriguez, OP
Thompson, CM
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 117 : 101 - 110
[17] SYNTHESIS OF STERICALLY HINDERED STRAPPED PORPHYRINS
LEE, CH
LEE, CK
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1992, 13 (04) : 352 - 354
[18] Synthesis of Sterically Hindered Phosphonamidothiolates and Phosphonamidodithioates
Phosphorus Sulphur Silicon Relat Elem, (101):
[19] STERICALLY HINDERED RESONANCE IN METHYL-SUBSTITUTED ANILINES IN THE GAS-PHASE
BOHM, S
DECOUZON, M
EXNER, O
GAL, JF
MARIA, PC
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26): : 8127 - 8131
[20] Synthesis of new organic phosphites containing sterically hindered, piperidine groups
Bauer, I
Habicher, WD
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1997, 128 : 79 - 103

← 1 2 3 4 5 →