Premium
PHOTOCHEMICAL AND FREE RADICAL INITIATED REACTIONS OF 1 ,3‐DIMETHYLTHYMINE WITH ISOPROPANOL
Author(s) -
Shetlar Martin D.
Publication year - 1979
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1979.tb07046.x
Subject(s) - chemistry , acetone , photochemistry , radical , thymine , cyclobutane , adduct , yield (engineering) , decomposition , quantum yield , benzoyl peroxide , uracil , medicinal chemistry , organic chemistry , monomer , dna , fluorescence , ring (chemistry) , biochemistry , materials science , physics , quantum mechanics , metallurgy , polymer
— A photochemically induced reaction of 1 ,3‐dimethylthymine (DMT) with isopropanol leads to the formation of four alcohol adducts. The products have been identified as the cis and trans isomers of 5 ,6‐dihydro‐1,3‐dimethyll‐6‐(2‐hydroxy‐2‐propyl) thymine (I and II), 2.4‐diaza‐8‐hydroxy‐2.4,6.8‐tetramethylbicyclo[4.2.0]octan‐1,3‐dione (III), and 5 ,6‐dihydro‐1,3‐dimethyl‐6‐(2‐oxo‐l‐propyl)‐thymine (IV). An acetone photosensitized reaction of DMT with isopropanol gives the same products in a similar relative yield distribution. In both of these reactions, cyclobutane dimers of DMT are produced as well. Free radical reactions of 2‐hydroxyisopropyl radicals with DMT, initiated by decomposition of di‐ t ‐butyl peroxide, leads to formation of only one of the cis and trans isomers described above. along with 1 ,3‐dimethyl‐5‐(2‐hydroxy‐2‐methyl‐1‐propyl)uracil (V).