1.3.5- trioxane alkane

Even with the limitation on yield implied by the statistical process, cross-dimerization is still useful when one of the reactants is an alkane, because the products are easy to separate, and because of the few other ways to functionalize an alkane. The cross-coupling of an alkane with trioxane is especially valuable, because hydrolysis of the product (10-6) gives an aldehyde, thus achieving the conversion RH RCHO. The mechanism probably involves abstraction of H by the excited Hg atom, and coupling of the resulting radicals. 

Trioxan gives a protected aldehyde as product. For example, the cross-dimer from trioxan and cyclohexane gives C6HuCHO on hydrolysis. The overall process is equivalent to an alkane carbonylation. Likewise, a protected form of prolinal is formed from trioxan and pyrrolidine. 

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