Tetrahedron
Tetrahedron
5 years ago

Nitrosocarbonyl hetero-Diels–Alder cycloaddition with 2-substituted 1,3-butadienes

Nitrosocarbonyl hetero-Diels–Alder cycloaddition with 2-substituted 1,3-butadienes
A study of the reactivity of 2-substituted 1,3-butadienes with nitrosocarbonyl compounds in the 4+2 cycloaddition has been carried out showing that the regioselectivity involves a delicate balance of steric and electronic effects. 2-Aryl 1,3-butadienes favor the distal isomer with the magnitude of preference ranging from 4:1 to 15:1 depending on the nature of the nitrosocarbonyl group. However, when bulky 2-substituted dienes are used the proximal isomer is formed preferentially. The results obtained, together with previous theoretical calculations and experimental data, provide further data to aid in synthetic planning.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402016312017

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