Novel synthetic method for N-allylcarbamates from allyl ethers using chlorosulfonyl isocyanate
作者:Ji Deuk Kim、Min Hee Lee、Min Jung Lee、Young Hoon Jung
DOI:10.1016/s0040-4039(00)00776-0
日期:2000.6
Various allyl ethers were converted into the corresponding N-allylcarbamates using chlorosulfonyl isocyanate (CSI) via the stable allylic carbocation rather than β-lactam through [2+2] cycloaddition. The reaction of cinnamyl methyl ether with CSI afforded only methyl N-cinnamylcarbamate at 0°C, but at 20°C, it produced a mixture of methyl N-cinnamylcarbamate and methyl N-(1-phenylprop-2-enyl)carbamate
使用氯磺酰基异氰酸酯(CSI)通过稳定的烯丙基碳正离子化而不是β-内酰胺通过[2 + 2]环加成将各种烯丙基醚转化为相应的N-烯丙基氨基甲酸酯。肉桂基甲基醚与CSI的反应在0°C时仅提供N-肉桂酸氨基甲酸酯,但在20°C时,生成了N-(肉桂基氨基甲酸甲酯)和N-(1-苯基丙-2-烯基)氨基甲酸甲酯的混合物。比例为2.7:1。