Photochemical rearrangements of 2-cyclohexenones

Photochemistry of ketones in solution. 53. Stereospecific triplet-state photorearrangements of chiral 2-cyclohexenones: type A lumiketone rearrangement and phenyl migrations

“…Kuhn-Roth Oxidation of (+)-3-(2-pentyl)cyclopent-2-en-l-one (19). A solution of 8.4 g (85 mmol) of Cr03 in 50 mL of HzO was left standing overnight and then filtered through a sintered-glass funnel.…”

Facial Selective Photoreduction of Steroids: Role of Zeolites

“…Testosterone acetate ( 1 ) and cholestenone ( 2 ) have earlier been established to exhibit a solvent-dependent photobehavior. , The reaction that is relevant to this report is photoreduction of the enone CC double bond. Irradiation of 1 and 2 in 2-propanol yields reduction products (∼15% conversion in 2 h) shown in Scheme 1. , In 2-propanol, addition of hydrogen to carbon-5 of the A ring occurs predominantly from the less-hindered α-face of the molecule.…”

Structure and absolute configuration of (–)-taylorione, a novel carbon skeletal sesquiterpene ketone of ent-1,10-seco-aromadendrane form, from Mylia taylorii(liverwort)

“…of liydrogen had been taken up, the reaction was stopped. The mixture was filtered, ancl the filtrate concentrated in Z ~U C U O to obtain a crude product which was chromatographed on silica gel to give the dihydro-ketone (10) (320 nig) as a light yellow oil, C1,H2, 0,Mf 220;m / e 220,177,162,149,121,107,55,and 43; vnlax. 1 725, 1415, 1 390, 1 380, and 1 363 cni-l; 6 0.93 and 1.12 (each 3 H, s), 1 67 (3 H , br s), and 2.03 (3 H, s ) ; A, , , , , , 212 nm (E 5 900).…”