TY - JOUR
T1 - Aziridines, 61 [1]
T2 - Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products
AU - Buchholz, Berthold Buchholz
AU - Onistschenko, Andreas Onistschenko
AU - Stamm, Helmut Stamm
AU - Lin, Pen Yuan
PY - 1993/4/1
Y1 - 1993/4/1
N2 - It is shown (1) that in most reactions of anilines 2 with 1-sulfonyl-2,2-dim ethylaziridines 1 both isomeric products 3 and 4 are formed, (2) that the “normal” product 4 obtained by attack on position 3 of 1 usually arises in a small or negligible amount that seems to decrease with decreasing basicity of 2, and (3) that the amount of 4 strongly increases w ith increasing steric demand of 2. Formation of 4 is explained by a lag of bond making in SN2.
AB - It is shown (1) that in most reactions of anilines 2 with 1-sulfonyl-2,2-dim ethylaziridines 1 both isomeric products 3 and 4 are formed, (2) that the “normal” product 4 obtained by attack on position 3 of 1 usually arises in a small or negligible amount that seems to decrease with decreasing basicity of 2, and (3) that the amount of 4 strongly increases w ith increasing steric demand of 2. Formation of 4 is explained by a lag of bond making in SN2.
KW - 1-Sulfonyl-2,2-dim ethylaziridines
KW - Basicity Effect
KW - N-Aryl-N′-sulfonyl-gem-dimethylethylenediamines
KW - Regioselectivity of Nucleophilic Ring Opening
KW - Steric Hindrance Effect
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U2 - 10.1515/znb-1993-0414
DO - 10.1515/znb-1993-0414
M3 - Article
AN - SCOPUS:84945050582
SN - 0932-0776
VL - 48
SP - 483
EP - 487
JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
IS - 4
ER -