23781-83-1

Upstream product

• 101269-60-7 4-phenyl-decahydro-azulene 
• 591-51-5 phenyllithium 
• 275-51-4 azulene 
• 1623-99-0 phenyl sodium 
• 14958-13-5 diethyl-buta-1,3-dienyl-amine 
• 7338-50-3 6-phenylfulvene 
• 108-86-1 bromobenzene 
• 313063-26-2 Diethyl 4-phenyl-1,4-dihydroazulene-1,3-dicarboxylate 
• 109596-17-0 1-(3-diazo-2-oxo-1-phenyl-propyl)-2-(3-diazo-2-oxo-propyl)-cyclopentane 
• 101604-65-3 3-phenyl-3,3'-cyclopentane-1,2-diyl-di-propionic acid 
• 106990-30-1 4-phenyl-octahydro-azulen-6-one 
• 36044-39-0 diethyl (azulene)-1,3-dicarboxylate 
• 50883-02-8 Diethyl 4-phenylazulene-1,3-dicarboxylate 
• 100-63-0 phenylhydrazine 

Downstream Products

• 101601-92-7 4-methyl-8-phenyl-azulene 
• 102467-61-8 4,8-diphenylazulene 

Relevant academic research and scientific papers

An analysis of the bonding properties of benz[a]azulene by X-ray, NMR, and computational studies

The X-ray crystal structures of 9-phenylbenz[a]azulene (4) and the corresponding non-benzannelated form, 4-phenylazulene (5), have been determined (cf. Fig. 2). In contrast to 5, the skeleton of which shows nearly equal C,C bond lengths (cf Table 1), the

Reactions of diethyl azulene-1,3-dicarboxylate derivatives and 1-azaazulene derivatives with Grignard reagents, and alkyl- and aryllithium

Reactions of diethyl azulene-1,3-dicarboxylate (1) and diethyl 2-chloroazulene-1,3-dicarboxylate (11) with Grignard reagents, followed by dehydration with tetrachloro-1,2-benzoquinone, gave 2-, 4,- and 6-substituted additionoxidation products. Grignards reagents have a tendency to react with 1 at the positions in the order of 2 > 4 > 6, while steric hindrance has a greater influence at the positions in order of 2 > 4 > 6. Reactions of 1 and 11 with phenyllithium and methyllithium gave similar results. On the other hand, on the reaction of diethyl 2-methoxy-azulene-1,3-dicarboxylate (15), Grignard reagents attacked preferentially at the methoxy group, and 2-substituted products were obtained. Use of excess molar equivalents of Grignard reagents led to diaryl-substituted products. Reaction of 2-chloro-1-azaazulenes with Grignard reagents also gave similar addition-oxidation products, and reacted at the positions in the order 8 ? 4 > 6, whereas reaction of 2-methoxy-1-azaazulene with a Grignard reagent gave 1-azaazulen-2(1H)-one. The Royal Society of Chemistry 2000.

ARYLATION OF AZULENE

In the reaction of azulene with phenylhydrazine and an oxidizing agent (Cu(2+)) a mixture of 1-phenylazulene (28percent) with 2-, 4-, and 6-phenylazulenes (27percent in total) is formed; a series of para-substituted phenylazulenes and α-naphthylazulenes were obtained in a similar way.If p-nitrophenylhydrazine is used, selective arylation of azulene (at position 1) and also of dimethylaniline (at the ortho and para positions) occurs.An excess of the oxidizing agent (Cu(2+)) increases and an excess of the reducing agent (arylhydrazine) reduces the selectivity of arylation.Some of the obtained arylazulenes can be used as dichroic coloring additives for liquid crystals.