4-Nitroso-l-octanol

The photolysis of 1-octyl nitrite 6 yields 4-nitroso-l-octanol 8 in 45% yield, via cyclic transition state 7—the formation of regioisomeric nitroso alcohols is not observed ... 

Photolysis of n-octylnitrite in solvents that are poor hydrogen donors (e.g., benzene) results primarily in the formation of the dimer of 4-nitroso-l-octanol. 

Photolysis of -octylnitrite in heptane solution results in formation of the dimers of 2-, 3-, and 4-nitrosoheptane as well as the dimer of 4-nitroso-l-octanol (intramolecular hydrogen abstraction)[Pg.559]

The involvement of an intramolecular hydrogen abstraction in the Barton reaction is not necessarily limited to those molecules with rigid stereochemistry. In fact, simple aliphatic nitrites undergo the Barton reaction with equal ease. Thus, the principal product obtained from the photolysis of ra-octyl nitrite20 in benzene solution is the dimer of 4-nitroso-l-octanol however, photolysis of n-octyl nitrite in n-heptane20 produced a mixture of 7/-nitroso heptanes in addition to 4-nitroso-l-octanol in the ratio l 4.5,f respectively. The formation of y-nitroso heptane obviously results from an attack of the intermediate alkoxy radical on the solvent molecule. The intermediate alkyl radical then collapses, according to eq. 2. For the sake of convenience we have indi-... 

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