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2005
Azide formation
O 0272
Radical Substitution with Azide: TMSN3—PhI(OAc)2 as a Substitute of IN3. —
azidonation of benzyl ethers, e.g. (I), acetals like (X) and aldehydes (XII) is
32- 062 The
smoothly achieved using low-valent PhI(O-Ac)2—TmsN3 instead of hazardous IN 3.
The reaction proceeds under mild conditions and is faster than with IN3. Use of chiral
auxiliaries as in (III) and (V) does not lead to significant diastereoselectivity. The azidonation of aldehydes (XII) gives unstable acyl azides. They are directly converted on
heating to Curtius rearrangement products, namely isocyanates, which undergo a further azidonation to finally afford carbamoyl azides (XIII). A plausible radical reaction
mechanism is presented. — (PEDERSEN, C. M.; MARINESCU, L. G.; BOLS*, M.;
Org. Biomol. Chem. 3 (2005) 5, 816-822; Dep. Chem., Univ. Aarhus, DK-8000
Aarhus, Den.; Eng.) — Mischke
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