Asgarova Aytan R, Khalilov Ali N, Brito Ivan, Maharramov Abel M, Shikhaliyev Namiq G, Cisterna Jonathan, Cárdenas Alejandro, Gurbanov Atash V, Zubkov Fedor I, Mahmudov Kamran T
Department of Chemistry, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan.
Departamento de Química, Universidad de Antofagasta, Avda. Universidad de Antofagasta 02800, Campus Coloso Antofagasta-Chile, Antofagasta 1240000, Chile.
Acta Crystallogr C Struct Chem. 2019 Mar 1;75(Pt 3):342-347. doi: 10.1107/S2053229619001025. Epub 2019 Feb 19.
Cooperative action of hydrogen and halogen bonding in the reaction of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one with HCl or HBr in alcohol medium under microwave irradiation (20 W, 80 °C, 10 min) allows the isolation of the haloetherification products (2S,3S)-3-(3-tert-butyl-5-chloro-4-hydroxyphenyl)-2-chloro-3-ethoxy-1-phenylpropan-1-one, CHClO, (2S,3S)-2-bromo-3-(3-tert-butyl-5-bromo-4-hydroxyphenyl)-3-methoxy-1-phenylpropan-1-one, CHBrO, and (2S,3S)-2-bromo-3-(3-tert-butyl-5-bromo-4-hydroxyphenyl)-3-ethoxy-1-phenylpropan-1-one, CHBrO, in good yields. Both types of noncovalent interactions, e.g. hydrogen and halogen bonds, are formed to stabilize the obtained products in the solid state.
在微波辐射（20瓦，80°C，10分钟）下，3-(3,5-二叔丁基-4-羟基苯基)-1-苯基丙-2-烯-1-酮与HCl或HBr在醇介质中反应时，氢键和卤键的协同作用使得能够分离出卤醚化产物(2S,3S)-3-(3-叔丁基-5-氯-4-羟基苯基)-2-氯-3-乙氧基-1-苯基丙-1-酮（CHClO）、(2S,3S)-2-溴-3-(3-叔丁基-5-溴-4-羟基苯基)-3-甲氧基-1-苯基丙-1-酮（CHBrO）和(2S,3S)-2-溴-3-(3-叔丁基-5-溴-4-羟基苯基)-3-乙氧基-1-苯基丙-1-酮（CHBrO），产率良好。两种类型的非共价相互作用，即氢键和卤键，形成以稳定固态下获得的产物。
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