Ring opening of 1,1-dinitrocyclopropane by addition of C, N, O and S nucleophiles

Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes

“…It is known, that nucleophilic ring opening of acceptor substituted cyclopropanes with pyridine furnishes betaine products. 20 Ring closure was expected to be more favored with electron deficient pyridines, as the positive charge of the betaine intermediate is then less stabilized. Indeed, the desired dearomative [3 + 2] annulation products of electron-deficient pyridines and 6a were isolated with good yield and high diastereoselectivity (>20 : 1) when the catalyst loading was raised to 10 mol% and the concentration to 1 M (Fig.…”

Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives

“…For instance, 1,1-dinitrocyclopropane is not affected when heated at 150 °C for 40−120 min. 29,286 For such substrates, the double nucleophilic displacement pathway can give excellent results, especially using an iodide source. F − , Cl − and Br − have also been reported to be competent.…”

“…b Ar = 2,6-di-tert-butyl-4-methoxyphenyl. of nucleophiles under comparatively mild conditions (Scheme 119) 286. Scheme 119.…”

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

“…73 Its reactions with primary, secondary, and tertiary amines were performed under very mild conditions and usually resulted in betaines 32 (Scheme 13). The reaction of 31 with weakly basic aniline proved to be the exception, yielding amine 33.…”