| SM ISO690:2012|
CIOCARLAN, Alexandru; ARICU, Aculina; BÎRÎIAC, Andrei; LUNGU, Lidia; EDU, Carolina; GRINCO, Marina; SHOVA, Sergiu. Photochemical transformation of methyl bicyclohomofarnesoates. In: Materials Science and Condensed Matter Physics. Editia a 7-a, 16-19 septembrie 2014, Chișinău. Chișinău, Republica Moldova: Institutul de Fizică Aplicată, 2014, p. 147.
|Materials Science and Condensed Matter Physics
Editia a 7-a, 2014
Conferința "Materials Science and Condensed Matter Physics" |
Chișinău, Moldova, 16-19 septembrie 2014
Photochemical transformations have attracted much attention in synthetic organic chemistry, because they are cheap and environmentally friendly. Nowadays the interest for homodrimanic compounds increases substantially and frequently their syntheses were performed starting from known methyl bicyclohomofarnesoates (1-3)  . We performed the tetraphenylporphyrin-sensitized photo-oxygenation of esters (1-3) mixture in methylene chloride. This conditions usually generates unstable and unseparable chromatographically allylic hydroperoxides and endoperoxide . For this reason the crud reaction product was reduced with NaBH4 in methanol in corresponding hydroxilated compounds without purification (Figure 1). Reported compounds dehydrolactone (4), ketodioxine (5) and epimeric hydroxydioxines (6) and (7) were isolated by column chromatography, their structure were confirmed by spectral methods (IR, 1H and 13C NMR) and finally by X-ray diffraction on monocrystals (Figure 2).