Green chemistry: Efficient epoxides ring-opening with 1-butanol under microwave irradiation

被引:10
作者
Garcia-Vidal, Jesus A.
Duran-Valle, Carlos J.
Ferrera-Escudero, Santiago
机构
[1] Univ Extremadura, Fac Ciencias, Dept Quim Inorgan, E-06071 Badajoz, Spain
[2] Univ Nacl Educ Distancia, Dept Quim Inorgan & Quim Tecn, E-28040 Madrid, Spain
关键词
epoxides; microwaves; activated carbon; catalysis;
D O I
10.1016/j.apsusc.2005.11.003
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Two activated carbons treated with mineral acids (HNO3 and sulfonitric mixture) have been tested as acid catalysts in the epoxides (1,2-epoxyhexane and styrene oxide) ring-opening reaction with 1-butanol under microwave (MW) irradiation. The mayor obtained product is that resulting of the alcohol addition to the most substituted carbon in the epoxide ring. The most active catalyst is that treated with sulfonitric mixture. The use of a MW oven allows achieving to the complete conversion of styrene oxide in only 2 min. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:6064 / 6066
页数:3
相关论文
共 11 条
[1]   Convergent highly stereoselective preparation of the C12-C24 fragment of macrolactin A [J].
Bonini, C ;
Chiummiento, L ;
Pullez, M ;
Solladié, G ;
Colobert, F .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5015-5022
[2]   Organic reactions catalyzed over solid acids [J].
Corma, A ;
Garcia, H .
CATALYSIS TODAY, 1997, 38 (03) :257-308
[3]   CsOH-promoted epoxide ring-opening with phosphines: mild and efficient synthesis of monohydroxyphosphines [J].
Fox, DL ;
Robinson, AA ;
Frank, JB ;
Salvatore, RN .
TETRAHEDRON LETTERS, 2003, 44 (41) :7579-7582
[4]   Practical synthesis of chiral ligands for catalytic enantioselective cyanosilylation of ketones and ketoimines [J].
Kato, N ;
Tomita, D ;
Maki, K ;
Kanai, M ;
Shibasaki, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :6128-6130
[5]   Microwave heating in the TS-1 catalyzed oxyfunctionalisation of n-hexane [J].
Kooyman, PJ ;
Luijkx, GCA ;
Arafat, A ;
vanBekkum, H .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 111 (1-2) :167-174
[6]   Microwave-assisted high-speed chemistry: a new technique in drug discovery [J].
Larhed, M ;
Hallberg, A .
DRUG DISCOVERY TODAY, 2001, 6 (08) :406-416
[7]   APPLICATIONS OF MICROWAVE-ACCELERATED ORGANIC-SYNTHESIS [J].
MAJETICH, G ;
HICKS, R .
RADIATION PHYSICS AND CHEMISTRY, 1995, 45 (04) :567-579
[8]   APPLICATIONS OF MICROWAVE DIELECTRIC HEATING EFFECTS TO SYNTHETIC PROBLEMS IN CHEMISTRY [J].
MINGOS, DMP ;
BAGHURST, DR .
CHEMICAL SOCIETY REVIEWS, 1991, 20 (01) :1-47
[9]   Efficient regio- and stereoselective ring opening of epoxides with alcohols, acetic acid and water catalyzed by ammonium decatungstocerate(IV) [J].
Mirkhani, V ;
Tangestaninejad, S ;
Yadollahi, B ;
Alipanah, L .
TETRAHEDRON, 2003, 59 (41) :8213-8218
[10]   New strategy for the construction of a monotetrahydrofuran ring in annonaceous acetogenin based on a ruthenium ring-closing metathesis:: Application to the synthesis of Solamin [J].
Prestat, G ;
Baylon, C ;
Heck, MP ;
Grasa, GA ;
Nolan, SP ;
Mioskowski, C .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5770-5773