Ring opening of 1 with pyridinium chloride or pyridinium iodide in chloroform and/or pyridine gives significant amounts of halohydrins 2a or 2b, reflecting partial suppression of the Wagner-Meerwein rearrangement that occurs on ring-opening with hydrogen halides. Opening with pyridinium iodide (but not with pyridinium chloride) in acetonitrile gave considerable amounts of the 2-endo-iodohydrin 4b. Pyridinium poly(hydrogen fluoride) or triethylammonium tris(hydrogen fluoride) gave only rearranged products. © 1983 American Chemical Society.
Pyridinium halide promoted ring-opening reactions of exo-norbornene oxide / G., Gargaro; Loreto, Maria Antonietta; Pellacani, Lucio; Tardella, Paolo Antonio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 48:(1983), pp. 2043-2046.
Pyridinium halide promoted ring-opening reactions of exo-norbornene oxide
LORETO, Maria Antonietta;PELLACANI, Lucio;TARDELLA, Paolo Antonio
1983
Abstract
Ring opening of 1 with pyridinium chloride or pyridinium iodide in chloroform and/or pyridine gives significant amounts of halohydrins 2a or 2b, reflecting partial suppression of the Wagner-Meerwein rearrangement that occurs on ring-opening with hydrogen halides. Opening with pyridinium iodide (but not with pyridinium chloride) in acetonitrile gave considerable amounts of the 2-endo-iodohydrin 4b. Pyridinium poly(hydrogen fluoride) or triethylammonium tris(hydrogen fluoride) gave only rearranged products. © 1983 American Chemical Society.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
