Synthesis and Evaluation of a Photochromic Surfactant for Organic Reactions in Aqueous Media

被引:36
作者
Drillaud, Nicolas [1 ]
Banaszak-Leonard, Estelle [1 ]
Pezron, Isabelle [1 ]
Len, Christophe [1 ]
机构
[1] Univ Technol Compiegne, EA UTC ESCOM 4297, Ctr Rech Royallieu, F-60205 Compiegne, France
关键词
ACYLATION; AMINES; WATER; TELOMERIZATION; BUTADIENE; REARRANGEMENT; CLEAVAGE; KETONES; SYSTEM; MILD;
D O I
10.1021/jo301466w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel photochromic azobenzene-based surfactant was described for organic chemistry in water. The molecule 4-butylazobenzyl-4'-triazologlucuronic acid sodium salt thus synthesized can be isomerized from its trans to its cis form reversibly in solution by simple light irradiation. That property allowed the recyclability of a model acetylation reaction performed in the surfactant media, compared to the well-known, commercially available sodium dodecyl sulfate surfactant media.
引用
收藏
页码:9553 / 9561
页数:9
相关论文
共 44 条
[1]  
Abbau der Reduzierenden Biosen, 1926, BIOCHEM, V59, P1254, DOI [10.1002/cber.19260590626, DOI 10.1002/CBER.19260590626]
[2]   Molecular iodine in isopropenyl acetate (IPA): a highly efficient catalyst for the acetylation of alcohols, amines and phenols under solvent free conditions [J].
Ahmed, Naseem ;
van Lier, Johan E. .
TETRAHEDRON LETTERS, 2006, 47 (30) :5345-5349
[3]  
Anastas P.T., 1998, Green chemistry: theory and practice
[4]   A Light-Controlled Molecular Brake with Complete ON-OFF Rotation [J].
Basheer, Meethale C. ;
Oka, Yoshimi ;
Mathews, Manoj ;
Tamaoki, Nobuyuki .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (11) :3489-3496
[5]   Amphiphilic photo-isomerisable phosphanes for aqueous organometallic catalysis [J].
Bricout, Herve ;
Banaszak, Estelle ;
Len, Christophe ;
Hapiot, Frederic ;
Monflier, Eric .
CHEMICAL COMMUNICATIONS, 2010, 46 (41) :7813-7815
[6]   Photofoams: Remote Control of Foam Destabilization by Exposure to Light Using an Azobenzene Surfactant [J].
Chevallier, E. ;
Monteux, C. ;
Lequewx, F. ;
Tribet, C. .
LANGMUIR, 2012, 28 (05) :2308-2312
[7]   Solvent-free reduction of aldehydes and ketones using solid acid-activated sodium borohydride [J].
Cho, Byung Tae ;
Kang, Sang Kyu ;
Kim, Min Sung ;
Ryu, Soo Ryeon ;
An, Duk Keun .
TETRAHEDRON, 2006, 62 (34) :8164-8168
[8]   Functionalized Organocatalytic Nanoreactors: Hydrophobic Pockets for Acylation Reactions in Water [J].
Cotanda, Pepa ;
Lu, Annhelen ;
Patterson, Joseph P. ;
Petzetakis, Nikos ;
O'Reilly, Rachel K. .
MACROMOLECULES, 2012, 45 (05) :2377-2384
[9]   Beckmann rearrangement of oximes under very mild conditions [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :6272-6274
[10]   Well-defined copper(I) complexes for Click azide-alkyne cycloaddition reactions: one Click beyond [J].
Diez-Gonzalez, Silvia .
CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (02) :166-178