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• W2096887156 abstract "Abstract The photochemical [2+2] cycloadditions (the Paternò–Büchi reaction) of 1,3‐dimethylthymine (DMT) or 1,3‐dimethyluracil (DMU) with benzophenone and its six 4,4′‐disubstituted derivatives (BPs) generate two series of regioisomeric oxetanes, the head‐to‐head ( hh ) oxetanes 2 or 4 and the head‐to‐tail ( ht ) oxetanes 3 or 5 . The PB reactions reveal notable substituent effects on their regioselectivity, photochemical efficiency as well as their stability and the mode of ring‐opening. The regioselectivity and the photochemical efficiency correlate clearly with the electronic properties of the substituents of the BPs, that is, the BPs with electron‐withdrawing groups (EWGs) give more efficient PB reactions with a lower proportion of the hh oxetane and less efficient PB reactions with a higher proportion of the hh oxetane for BPs with electron‐donating groups (EDGs). The oxetanes from DMT, 2 and 3 , are more stable than the corresponding oxetanes from DMU, 4 and 5 . The oxetanes from the BPs with EWGs are more stable than the corresponding oxetanes formed from the BPs with EDGs. The ring‐opening modes of the oxetanes are also dependent on the DMT/DMU and BPs in the presence of acid.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)" @default.
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• W2096887156 date "2006-03-14" @default.
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• W2096887156 title "The Paternò–Büchi Reaction of 1,3‐Dimethyluracil and 1,3‐Dimethylthymine with 4,4′‐Disubstituted Benzophenones" @default.
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• W2096887156 doi "https://doi.org/10.1002/ejoc.200500862" @default.
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