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• W2325593226 endingPage "8220" @default.
• W2325593226 startingPage "8212" @default.
• W2325593226 abstract "The reaction of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with acenaphthylene and indene leads not only to the formation of the expected [2 + 2] diazetidine cycloadducts but also to unexpected 2:1 adducts of MeTAD with substrate. The structures of the products derived from acenaphthylene were confirmed by X-ray crystallography. A similar distribution of products was afforded from indene. The 2:1 adducts appear to derive from a diradical intermediate, the radical centers of which are strongly stabilized by the bridging urazoyl ring and benzylic delocalization. The triplet states of these diradical intermediates may be trapped via exposure to molecular oxygen to afford oxygen-containing adducts. Computational studies at the (U)B3LYP/6-31G* level provide additional support for the conclusions of our experimental work." @default.
• W2325593226 created "2016-06-24" @default.
• W2325593226 creator A5024279196 @default.
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• W2325593226 creator A5039300415 @default.
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• W2325593226 creator A5082054439 @default.
• W2325593226 date "2014-08-07" @default.
• W2325593226 modified "2023-09-29" @default.
• W2325593226 title "Unexpected σ Bond Rupture during the Reaction of N-Methyl-1,2,4-triazoline-3,5-dione with Acenaphthylene and Indene" @default.
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• W2325593226 doi "https://doi.org/10.1021/jo5014096" @default.
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• W2325593226 hasPublicationYear "2014" @default.
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