|
Functional organic molecular design has a very important significance in organic synthesis process , multi- shrink ring compounds in organic electroluminescent conductive material such as organic functional materials has good application prospects . Therefore, based on 1,6 - methylene-bridged [ 10 ] annulene skeleton shrink ring synthesis and properties of great significance. The present study , during the synthesis , 4 - bromo- 1,6 - methylene bridge [ 10 ] annulene -3 - ethyl acetate as raw material, obtained by LiAlH4 reduction of 3 - hydroxymethyl-4- bromo-1 , 6 - methylene [ 10 ] annulene , in a yield of 82% , and PBr3 bromination reaction of the bromide obtained in the yield was 82 % , and the reaction was carried out PPh3 , is obtained quantitatively based on the 1,6 - methylenedioxy yl - bridge [ 10 ] annulene Wittig salt in the presence of a base , with a variety of aromatic aldehydes Wittig reaction to give the cis and a trans body 3 - substituted aromatic -4 - bromo - 1,6 - methylene bridge [ 10 ] annulene mixture . New cis-trans structure transformation : in the light conditions , a mixture of cis and trans isomers of cis body with iodine , benzene stirred for 3 h , 98 % conversion rate converted to trans body , cis olefin trans isomerization transformed to provide a simple method . Catalyzed by palladium salt , trans 3 - aromatic substitution -4 - bromo 1,6 - methylene bridge [ 10 ] annulene intermolecular Heck coupling reaction , the series is based on 1,6 - methylene bridge [ 10 ] annulene skeleton shrink ring compounds . The structure of the resulting compounds were characterized by IR, 1H NMR, 13C NMR and MS spectra .
|