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Photochemische Reaktionen. 56. Mitteilung [1]. Die Photoisomerisierung des α,β‐ungesättigten δ‐Diketons 3, 7‐Dioxo‐4, 4‐dimethyl‐17 β‐acetoxy‐δ 5 ‐androsten und dessen 3‐Ketalderivates
Author(s) -
Domb S.,
Bozzato G.,
Saboz J. A.,
Schaffner K.
Publication year - 1969
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19690520825
Subject(s) - chemistry , isomerization , quenching (fluorescence) , naphthalene , irradiation , ethylene , photochemistry , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , fluorescence , catalysis , physics , quantum mechanics , nuclear physics , financial economics , economics
Abstract On irradiation with light of wavelengths 2537 or > 3400 Å 4,4‐dimethyl‐17β‐acetoxy‐androst‐5‐ene‐3, 7‐dione ( 8 ) rearranges to the two diastereoisomeric products 9 and 10 . This isomerization is the only detectable photochemical reaction of 8 in a variety of solvents, including p ‐dioxane. Complete quenching with 0.5M naphthalene (on irradiation with > 3400 Å) indicates a triplet reaction. The photochemistry of the 3‐ethylene ketal derivative 29 differs completely. Irradiation in p ‐dioxane solution leads exclusively to photoreduction and formation of the four diastereoisomeric dioxanyl allyl tert .‐carbinols 30a – d .