Article ID Journal Published Year Pages File Type
5230152 Tetrahedron 2007 7 Pages PDF
Abstract

Cycloadducts 3 and 4 were treated with tetrabutylammonium fluoride and rapidly suffer cleavage on the three-membered ring to form either pyridin-4(1H)-one or 1H-azepin-4(7H)-one. When R1 is an oxycarbonyl or a 2-pyridyl group and R2 is a negative charge-stabilizing group (cases 3a,b and 4f) the C-C bond cleaves forming products 5. However, when R2=H (case 3c) the ring expands to seven members. When R1 is an acyl group the pyridin-4(1H)-one formation includes an unexpected shift of the carbonyl group.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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