103723-80-4Relevant academic research and scientific papers
Intramolecular 'Ene' Reactions of Transient, Allylic, and Homoallylic C-Nitrosoformate Esters
Kirby, Gordon W.,McGuigan, Henry,McLean, David
, p. 1961 - 1966 (2007/10/02)
Various allylic and homoallylic alcohols have been treated succesively with phosgene and hydroxylamine to form the corresponding N-hydroxycar bamic esters (3).Oxidation of these hydroxamic acid derivatives with sodium or tetraethylammonium periodate in the presence of cyclopentadiene gave the cycloadducts (5) derived from transient allylic and C-nitrosoformate esters (4) and cyclopentadiene.When the cycloadducts were heated in benzene at 80 degree C, or toluene at 111 degree C, they dissociated and the C-nitrosoformate esters underwent intramolecular 'ene' reactions to give hydroxamic acid derivatives having newly formed, five- six- or seven-membered heterocyclic rings.
