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19.7.1.1.5.2 Variation 2: With Trichloromethyl Chloroformate (Diphosgene)

DOI: 10.1055/sos-SD-019-00308

Suginome, M.; Ito, Y.Science of Synthesis, (200419457.

Trichloromethyl chloroformate (diphosgene) is a safer alternative to phosgene and is similarly effective for the dehydration of N-substituted formamides in the synthesis of isocyanides 30.[‌43‌] In many cases, higher yields have been achieved with the diphosgene method than with the phosgene method. Preparations of some selected isocyanides are summarized in Scheme 19. For the synthesis of isocyanides from optically active amino acid derivatives, the use of 4-methylmorpholine as a base is recommended to avoid racemization.

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