Publication: An unexpected transformation of benzyl carbamates into alpha-azidobenzeneacetamides
An unexpected transformation of benzyl carbamates into alpha-azidobenzeneacetamides
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Strässler, C., & Heimgartner, H. (1997). An unexpected transformation of benzyl carbamates into alpha-azidobenzeneacetamides. Helvetica Chimica Acta, 80, 2058–2065. https://doi.org/10.1002/hlca.19970800706
Abstract
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Abstract
Successive treatment of benzyl carbamates 5 (Z-protected secondary amines) with lithium diisopropylamide (LDA), diphenyl phosphorochloridate (DPPCl), and NaN3 yielded the corresponding alpha-azidobenzeneacetamides 6 in 45-50% yield (Schemes 2 and 3). In the case of Z-protected diisopropylamine 5b, the phosphate 7 was isolated as a minor product. A reaction mechanism for this unexpected transformation is proposed in Scheme 4, the key step being the ring closure of a benzylic anion to give an oxirane intermediate B. In cursory experimen
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- Strässler, Christof
- Heimgartner, Heinz
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Strässler, C., & Heimgartner, H. (1997). An unexpected transformation of benzyl carbamates into alpha-azidobenzeneacetamides. Helvetica Chimica Acta, 80, 2058–2065. https://doi.org/10.1002/hlca.19970800706
