Tetrahedron

Rearrangement of nitrones to amides using chlor0sulfonyl isocyanate

SP Joseph, DN Dhar

Index: Joseph, Sajan P.; Dhar, D. N. Tetrahedron, 1986 , vol. 42, # 21 p. 5979 - 5983

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Citation Number: 10

Abstract

Reaction of chlorosulfonyl isocyanate (CSI) with nitrones 1 an and 5 a, b has been studied. α, α, N-Triaryl nitrones 1 an react with CSI to form the N, N-diaryl arylamides 3 an and 4 in in good yields. In the case of α-H, α, N-diaryl nitrones 5 a, b however, two compounds viz., the rearranged product 11 a, b and the 1, 4-dihydro tetrazines 10 a, b are formed. The effect of substituents on the rearrangement has been studied. It is found that the nature of the ...