Abstract
Irradiation of ethyl azidoformate dissolved in cyclic ethers (IIIA-VA) and acetals (VIA-VIIIA) yields insertion products (IIIB-VIIIB) of carboethoxynitrenes (II S and II T). The attack of the nitrenes occurs exclusively at the CH bond adjacent to the ether oxygen or adjoining acetal oxygens to produce a single insertion product in each case. Byproducts are urethane (IX) and the dimerization product (X) of amino radicals (XI). The effects of acetophenone as a sensitizer and of methylene chloride as a diluent have been examined and discussed. Reduction of IIIB and IVB with LAH produces 4-methylaminobutan-1-ol and 5-methylaminopentan-1-ol in 62 and 83% yields, respectively.
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