Formation of 4-Nitrocyclohexa-2,5-dienols by Addition of Organolithium Reagents to 4-Alkyl-4-nitrocyclohexa-2,5-dienones

Article abstract of DOI:10.1021/jo00229a007

Addition of methyllithium to 4-alkyl-4-nitrocyclohexa-2,5-dienones 1a-d (alkyl = Me, Et, i-Pr, t-Bu), to 2,6-dichloro- and 2,6-dibromo-4-methyl-4-nitrocyclohexa-2,5-dienone, and to 4a-nitro-2-oxo-2,4a,5,6,7,8-hexahydronaphthalene gives the corresponding dienols 2a-d, 4e and 4f, and 7g, generally as a pair of diastereomers.Addition of methyl lithioacetate to the same substrates gives dienols 8a-d, 5e and 5f, and 7h.Addition of substituted methyllithiums (XCH2Li, X = CN, CONH2, CONMe2, COMe, SMe, SPh, SOMe, SO2Me, SiMe3, PSMePh, PSPh2), 2-lithio-1,3-dithiane, or lithium phenylacetylide to 1a gives the dienols 9i-u.