ORGLIST: Hofmann rearrangement

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From: Witold Mozga (mozgaw$##$rocketmail.com)
Date: Thu Jul 08 1999 - 11:17:38 EDT

Hi everybody!

I intended to transform Boc-Asparagine into
Boc-Diaminepropionic acid by means of classical
Hofmann rearrangement. I knew that milder methods had
been developed (for example use of
bis-trifluoroacetoxyiodobenzene) but I wanted to test
the classical methodology employing 1 eqiv. of
bromine and excess alkali. Reaction proceeded very
fast, but during quenching with 6N HCl I observed
vigorous gas evolution. The smell resembles that of
cyclohexene. What happens? I don`t think that Boc can
be cleaved in this conditions because quenching was
careful and pH did not fall below 3.

Thanks in advance,

Witold Mozga































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