- Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers
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The stability order of various alkyl, allyl, and benzyl carbocations was investigated using the novel technique for comparing the stability of carbocations in solution developed by using a simple CSI reaction with various ethers. The p-methoxycinnamyl carbocation was the most stable in our reaction system and the next stable carbocation was the p-methoxybenzyl carbocation. The stability of the other carbocations decreased with methacryl, t-butyl, cinnamyl, acryl, benzyl, 2° and allyl carbocations in that order.
- Kim, Ji Duck,Han, Gyoonhee,Jeong, Lak Shin,Park, Hyun-Ju,Zee, Ok Pyo,Jung, Young Hoon
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p. 4395 - 4402
(2007/10/03)
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- Novel synthetic method for N-allylcarbamates from allyl ethers using chlorosulfonyl isocyanate
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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-(l-phenylprop-2-enyl)carbamate in a 2.7:1 ratio. (C) 2000 Elsevier Science Ltd.
- Kim, Ji Deuk,Lee, Min Hee,Lee, Min Jung,Jung, Young Hoon
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p. 5073 - 5076
(2007/10/03)
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