An improved synthesis of iodohydrins from alkenes

被引:47
作者
Smietana, M
Gouverneur, V
Mioskowski, C
机构
[1] CNRS, Lab Synth Bioorgan, F-67401 Illkirch Graffenstaden, France
[2] Univ Strasbourg 1, Fac Pharm, F-67401 Illkirch Graffenstaden, France
[3] New Chem Lab, Oxford OX1 3QT, England
关键词
iodohydrins; N-iodosuccinimide;
D O I
10.1016/S0040-4039(99)02022-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of iodohydrins was prepared in excellent yields in a one-step procedure by treating the corresponding alkenes at -20 degrees C with NIS in a mixture of H2O and DME. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:193 / 195
页数:3
相关论文
共 21 条
[1]   A FACILE ROUTE TO IODOHYDRINS AND EPOXIDES BY OXIDATION OF OLEFIN-IODINE COMPLEXES WITH PYRIDINIUM DICHROMATE [J].
ANTONIOLETTI, R ;
DAURIA, M ;
DEMICO, A ;
PIANCATELLI, G ;
SCETTRI, A .
TETRAHEDRON, 1983, 39 (10) :1765-1768
[2]   REACTIONS OF ALKENES WITH ELECTROPHILIC IODINE IN TETRAMETHYLENE SULFONE-CHLOROFORM [J].
CAMBIE, RC ;
NOALL, WI ;
POTTER, GJ ;
RUTLEDGE, PS ;
WOODGATE, PD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (03) :226-230
[3]   Mild and regiospecific nuclear iodination of methoxybenzenes and naphthalenes with N-iodosuccinimide in acetonitrile [J].
Carreno, MC ;
Ruano, JLG ;
Sanz, G ;
Toledo, MA ;
Urbano, A .
TETRAHEDRON LETTERS, 1996, 37 (23) :4081-4084
[4]  
Conforth J. W., 1970, J CHEM SOC C, P846
[5]   Stereoselective radical carbon-carbon bond forming reactions of beta-alkoxy esters: Atom and group transfer allylations under bidentate chelation controlled conditions [J].
Guindon, Y ;
Guerin, B ;
Chabot, C ;
Ogilvie, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (50) :12528-12535
[6]  
HANESSIAN S, 1981, SYNTHESIS-STUTTGART, P394
[7]   THE REACTION OF CARBONYL-COMPOUNDS WITH DIIODOMETHANE IN THE PRESENCE OF SAMARIUM - NOVEL SYNTHESES OF IODOHYDRINS AND CYCLOPROPANOLS [J].
IMAMOTO, T ;
TAKEYAMA, T ;
KOTO, H .
TETRAHEDRON LETTERS, 1986, 27 (28) :3243-3246
[8]   A NEW SYNTHETIC METHOD OF PREPARING IODOHYDRIN AND BROMOHYDRIN DERIVATIVES THROUGH IN-SITU GENERATION OF HYPOHALOUS ACIDS FROM H5IO6 AND NABRO3 IN THE PRESENCE OF NAHSO3 [J].
MASUDA, H ;
TAKASE, K ;
NISHIO, M ;
HASEGAWA, A ;
NISHIYAMA, Y ;
ISHII, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5550-5555
[9]   N-IODOSUCCINIMIDE-MEDIATED CONVERSION OF ALDEHYDES TO METHYL-ESTERS [J].
MCDONALD, C ;
HOLCOMB, H ;
KENNEDY, K ;
KIRKPATRICK, E ;
LEATHERS, T ;
VANEMON, P .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1213-1215
[10]   A MILD METHOD FOR THE PREPARATION OF FUNCTIONALIZED, UNSYMMETRICAL KETENE ACETALS [J].
MIDDLETON, DS ;
SIMPKINS, NS .
SYNTHETIC COMMUNICATIONS, 1989, 19 (1-2) :21-29