1,1-Dimethoxy-2,6-diphenyl-λ5-phosphorin-4-carbaldehyde and -4-carbonitrile

✍ Scribed by Dr. Hans Henning Pohl; Prof. Karl Dimroth

• Publisher: John Wiley and Sons
• Year: 1975
• Tongue: English
• Weight: 124 KB
• Volume: 14
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.197501111

✦ Synopsis

A well stirred solution of 3-methyllumiflavin~"1 (1.50g, 5.5 mmol) and N,N-dimethylpropargylamine (4.6 g, 55.0 mmol) in 0.1 M phosphate buffer (600 ml, pH 7.7) was illuminated under argon for 30 hours with a 170 W mercury high-piessure lamp (HERAEUS, Hanau; pyrex cooling jacket). The brown precipitate was filtered off by suction, washed with water (50ml), dried, and extracted with hot benzene (3 x 50ml). The residue was reprecipitated from hot chloroform (25 ml) by addition of hot benzene (60ml), and then from hot methanol (30 ml) by addition of ether (1 20 ml).

Yield : 600 mg (28 %) 5-(y-dimethyliminiopropenyl)-3-methyl-1,5-dihydrolumiflavin betaine; yellow needles, m. p. 226-227°C (dec.). UV: h,,, (E) in benzene 430nm (29650); in chloroform 427nm (22700); in methanol 402nm (25500); in H20, pH 7.0, 391 nm (25500). 'H-NMR (90 MHz; TMS as internal standard), 6 [ppm] in D,-DMSO: rotamer ( 3 n )