Tetrahedron Letters

Novel synthetic method for N-allylcarbamates from allyl ethers using chlorosulfonyl isocyanate

JD Kim, MH Lee, MJ Lee, YH Jung

Index: Kim, Ji Deuk; Lee, Min Hee; Lee, Min Jung; Jung, Young Hoon Tetrahedron Letters, 2000 , vol. 41, # 26 p. 5073 - 5076

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Citation Number: 25

Abstract

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 in a 2.7: 1 ratio.

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