Reaction of NO with Organic Compounds

On the other hand, benzyl ethers react with NO in the presence of the NHPI catalyst to afford the corresponding aromatic aldehydes (Eq. (6.29)) [170]. The reaction of 4-methoxymefhyltoluene catalyzed by NHPI (10mol%) under NO (1 atm) for 5 h leads to p-tolualdehyde in 50% yield, tert-Butoxymethyltoluene and terf-butyl benzyl ethers are converted into the corresponding aldehydes in good yields. 

The most important application of this procedure is the transformation of ethers to benzenedicarbaldehydes, which are attractive starting materials in pharmaceutical synthesis [173]. l,3-Dihydro-2-benzofuran and 1,3-di-terf-butoxymethyl- and 

4-dimethoxymethylbenzenes are converted into the respective dialdehydes in good yields (Eq. (6.30)) [170]. Of the various indirect procedures to obtain dialdehydes, hydrolysis of a,a,a, a -tetrabromoxylenes is usually used, although the preparation of bromides is troublesome [174]. Therefore, the present procedure provides a very convenient and direct route to benzenedicarbaldehydes. 

---

Platt, U., G. Le Bras, G. Poulet, J. P. Burrows, and G. Moortgat, Peroxy Radicals from Nighttime Reaction of NO, with Organic Compounds, Nature, 348, 147-149 (1990). 

---