Study Of Synthesis And Properties Of Multi-ring Compounds Based On 1,6-methano[10]annulene

The organic functional Materials are very important in organic chemical. They get more and more applications in materials science. Multi-ring compounds play a very important role such as organic luminescent materials and organic conductive materials. Therefore the study of Multi-ring compounds based on 1,6-methano[10]annulene is significance.The multi-ring compounds based on 1,6-methano[10]annulene was synthesized from ethyl 4-bromo-1,6-methano[10]annulene-3-carboxylate by a five-step reaction. The starting material ethyl 4-bromo-1,6-methano[10]annulene-3-carboxylate was reduced by LiAlH4 to obtain 3-hydroxymethyl-4-bromo-1,6-methano[10]annulene in 82%yield. 3-bromomethyl-4- bromo-1,6-methano[10]annulene was obtained with 3-hydroxymethyl-4-bromo-1,6-methano[10]annulene and PBr3 by bromination in ice-water bath, Then Wittig salt was proposed by reaction of 3-bromomethyl-4-bromo-1,6-methano[10]annulene with PPh3 refluxing in benzene,3-(p-aryl)-4-bromo-1,6-methano[10]annulenes were synthesized with Wittig salt and kinds of aromatic aldehyde by wittig reaction.3-(p-aryl)-4-bromo-1,6-methano[10]annulene reacts to give 12,13-bis(p-aryl)-12,13-dihydro-benzo[3,4-a;3',4'-d]bis-1,6-methano[10] annulenes by intermolecular coupling reaction under palladium catalyst.We first used the way that the cis- was photoisomerized trans- by irradiating solutions in benzene in the presence of I2, then the cis-converse to trans- by 98% conversion.The stucture of compounds were confirmed by IR,'H NMR,13C NMR and MS spectroscopy...