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Control of Regioselectivity by the l one Substituent through Steric and Electronic Effects in the Nitrosoarene Ene Reaction of Deuterium-Labeled Trisubstituted Alkenes

2002; American Chemical Society; Volume: 67; Issue: 24 Linguagem: Inglês

10.1021/jo026198i

1520-6904

Waldemar Adam, Oliver Krebs, Michael Orfanopoulos, Manolis Stratakis,

Fullerene Chemistry and Applications

For the ene reaction of 4-nitronitrosobenzene (ArNO) with a variety of primary and secondary lone alkyl-substituted substrates, the twix/twin regioselectivity is constant at about 85:15. In contrast, for the lone tert-butyl group and for lone aryl substituents, the twix regioisomer is obtained exclusively. These regioselectivities have been rationalized in terms of steric interactions and coordination between the enophile and the substrates in the transition states of the first reaction step.