OXYGEN YLIDES-II. PHOTOCHEMICAL AND RHODIUM-CATALYZED REACTIONS OF DIAZOMETHANE WITH (S)-2-METHYLOXETANE

Article abstract of DOI:10.1016/S0040-4039(00)61878-6

Photolysis of diazomethane in (S)-2-methyloxetane gives 2- and 3-methyltetrahydrofuran (1:3.2), the latter being formed with 21 percent net retention of configuration.In contrast, rhodium acetate catalysis yields racemic 3-methyltetrahydrofuran exclusively.