Nitrites, photolysis Barton reaction

Barton Reaction (Barton Nitrite Photolysis Reaction)... 

The Barton nitrite photolysis reaction involves the conversion of a nitrite ester 1 to a y-oximino-alcohol 3 by photolysis involving the homolytic cleavage of a nitrogen oxygen bond followed by hydrogen abstraction. ... 

The Barton nitrite photolysis reaction has played an important role in the synthesis of natural products and has been previously reviewed. The invention of this reaction enabled chemists to convert remote, un-activated, sp hybridized carbon atoms on conformationally constrained hydrocarbons. 

The Barton nitrite photolysis reaction also had an important role in terpene synthesis and the elucidation of terpene stmcture. For example, in Corey s syntheses of azadiradione and perhydrohistrionicotoxin " selective functionalization by means of the nitrite photolysis reaction was the crucial... 

Recently, Nakano and co-authors have utilized the Barton nitrite photolysis reaction in the synthesis of chiral ligands for catalysts A pseudoenantiomer of P-isocupreidine (P-ICD), was synthesized from quinine by employing a Barton nitrite photolysis reaction of the nitrite 40 to form the oxime 41. 

A recent patent application disclosed a method for making polyurethanes made from nitrite esters and di/poly-isocyanates with the help of UV-irradiation for use as coatings. The application disclosed polymerizable and curable compositions and processes of polymerizing and curing polyurethanes involving an isocyante compound and a nitrite ester compound. Irradiation of the nitrite ester compound with UV generates an active hydrogen compound by the Barton nitrite photolysis reaction that reacts with an isocyanate compound to produce and/or crosslink a polyurethane. 

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