Stereochemistry of protonation at C(1) of nitronate adducts from 1,6-conjugate addition of Grignard reagents to 2-methoxy-1-nitronaphthalene

Conjugated Nitrodienes. Synthesis and Reactivity

“…Bartoli et al , have studied conjugate additions between organometallic reagents and 104 or 1-nitronaphthalene . After treatment with a MeCOOH–MeCOOK buffer solution, the products (70–78% yields) were cis -9-alkyl-10-nitro-9,10-dihydroanthracenes 109 and mixtures of cis - and trans -4-alkyl-2-methoxy-1-nitro-1,4-dihydronaphthalenes 110 (Figure ).…”

“…58 The similarity between 1-substituted 1,3butadienes and 9-substituted anthracenes prompted the reinvestigation 59 of the Diels−Alder reactivity of 9-nitroanthracene (104) with acrylic acid (105) or acrylonitrile (106). The corresponding products were obtained as a mixture Bartoli et al 60,61 have studied conjugate additions between organometallic reagents and 104 60 or 1-nitronaphthalene. 61 After treatment with a MeCOOH−MeCOOK buffer solution, the products (70−78% yields) were cis-9-alkyl-10-nitro-9,10dihydroanthracenes 109 and mixtures of cis-and trans-4-alkyl-2methoxy-1-nitro-1,4-dihydronaphthalenes 110 (Figure 3).…”

“…The corresponding products were obtained as a mixture Bartoli et al 60,61 have studied conjugate additions between organometallic reagents and 104 60 or 1-nitronaphthalene. 61 After treatment with a MeCOOH−MeCOOK buffer solution, the products (70−78% yields) were cis-9-alkyl-10-nitro-9,10dihydroanthracenes 109 and mixtures of cis-and trans-4-alkyl-2methoxy-1-nitro-1,4-dihydronaphthalenes 110 (Figure 3). Functionalized 1,4-dihydronaphthalenes have been obtained through an inverse electron-demand aryne Diels−Alder reaction with acyclic dienes bearing electron-withdrawing substituents.…”