Nitrenes—XIV : Triethyl phosphite deoxygenation of α-(6-nitroveratrylidene)-γ-butyrolactone

Triethyl phosphite reduction of α-(6- nitroveratrylidene) - γ - butyrolactone (6) produced a mixture of 3,4 - dihydro - 7,8 - dimethoxy1.3]oxazino3.4-a]indol - 1 - one (8), ethyl 5,6 - dimethoxyindole - 2 - carboxylate (9) and 2,3 - dihydro - 6,7 - dimethoxyfuro2.3-b]quinoline (10). Photolysis of the corresponding 6-aminoveratrylidene derivative 11 also produced 10. Probable mechanisms and spectral evidence for the trans -configuration of 6 and 11 are presented.Nitration of α - veratrylidene - γ - butyrolactone (5) afforded not only the mononitro compound 6 but also a low yield of α - (α - nitrato - 6 - nitroveratryl) - α - nitro - γ - butyrolactone (7).