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|Title:||Regiospecific conversion of oxiranes, oxetanes, and lactones into difunctional nitrogen compounds via aminosilanes and aminostannanes||Authors:||Papini, A.
|Issue Date:||1984||Project:||None||Journal:||JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I||Abstract:||
nsertion reactions of Me3SiNEt2 (I) and Me3SnNEt2 (II) into oxirane, oxetane, and lactone rings were examd. The Et2AlCl- or AlCl3-catalyzed reactions of monoalkyloxiranes and monoalkyl- or aryloxetanes gave regioisomerically pure β- and γ-amino alcs., resp.; with polysubstituted oxiranes a low of regioselectivity was generally obsd. Ring-opening reactions of the lactone rings with I gave β-amino acids or ω-hydroxy amides, depending on the ring size. With II, spontaneous ring cleavage of alkyloxiranes and of β-propiolactone occurred with reverse regioselectivity, whereas oxetanes and γ- and δ-lactones were opened with the same regioselectivity as that obtained with I for these systems.
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