Transformation of Tertiary Benzyl Alcohols into the Vicinal Halo-Substituted Derivatives Using N-Halosuccinimides

被引:11
作者
Ajvazi, Njomza [1 ,2 ]
Stavber, Stojan [1 ,2 ,3 ]
机构
[1] Jozef Stefan Inst, Dept Phys & Organ Chem, Jamova 39, Ljubljana 1000, Slovenia
[2] Jozef Stefan Int Postgrad Sch, Jamova 39, Ljubljana 1000, Slovenia
[3] Jozef Stefan Inst, Ctr Excellence Integrated Approaches Chem & Biol, Jamova 39, Ljubljana 1000, Slovenia
关键词
halohydrins; halogenation; water; tertiary alcohols; N-halosuccinimides; VIC-HALOHYDRINS; STEREOSELECTIVE-SYNTHESIS; ORGANIC-CHEMISTRY; WATER; OLEFINS; SOLVENT; FLUORINATION; BROMINATION; F-TEDA-BF4; CONVERSION;
D O I
10.3390/molecules21101325
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The efficiency of direct conversion of tertiary alcohols bearing a beta-hydrogen atom to vicinal halohydrins-chlorohydrins and bromohydrins-under green reaction conditions was tested preliminarily on model tertiary benzyl alcohols. Tertiary alcohols were successfully directly halogenated to vicinal halohydrins with N-halosuccinimide in aqueous media. The efficiency of the reaction in water was significantly improved in the presence of sodium dodecyl sulphate as the surfactant.
引用
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页数:9
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共 38 条
[1]   Halohydrin and oxime derivatives of radicicol: Synthesis and antitumor activities [J].
Agatsuma, T ;
Ogawa, H ;
Akasaka, K ;
Asai, A ;
Yamashita, Y ;
Mizukami, T ;
Akinaga, S ;
Saitoh, Y .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) :3445-3454
[2]  
Anastas P., 1998, GREEN CHEM THEORY PR
[3]   Thiourea catalysis of NCS in the synthesis of chlorohydrins [J].
Bentley, Paul A. ;
Mei, Yujiang ;
Du, Juan .
TETRAHEDRON LETTERS, 2008, 49 (08) :1425-1427
[4]   REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES [J].
BONINI, C ;
RIGHI, G .
SYNTHESIS-STUTTGART, 1994, (03) :225-238
[5]   Green solvents for green technologies [J].
Bubalo, Marina Cvjetko ;
Vidovic, Senka ;
Redovnikovic, Ivana Radojcic ;
Jokic, Stela .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2015, 90 (09) :1631-1639
[6]   What is a green solvent?: A comprehensive framework for the environmental assessment of solvents [J].
Capello, Christian ;
Fischer, Ulrich ;
Hungerbuehler, Konrad .
GREEN CHEMISTRY, 2007, 9 (09) :927-934
[7]   Ammonium acetate catalyzed improved method for the regioselective conversion of olefins into halohydrins and haloethers at room temperature [J].
Das, Biswanath ;
Venkateswarlu, Katta ;
Damodar, Kongara ;
Suneel, Kanaparthy .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 269 (1-2) :17-21
[8]   Green Solvents in Carbohydrate Chemistry: From Raw Materials to Fine Chemicals [J].
Farran, Angeles ;
Cai, Chao ;
Sandoval, Manuel ;
Xu, Yongmei ;
Liu, Jian ;
Hernaiz, Maria J. ;
Linhardt, Robert J. .
CHEMICAL REVIEWS, 2015, 115 (14) :6811-6853
[9]   En route to full implementation: driving the green chemistry agenda in the pharmaceutical industry [J].
Federsel, Hans-Juergen .
GREEN CHEMISTRY, 2013, 15 (11) :3105-3115
[10]   REACTION OF BROMINE WITH PHENYL-SUBSTITUTED TERTIARY ALCOHOLS [J].
GRANT, DW ;
SHILTON, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (01) :135-137