Abstract
A new, mild procedure for the Hofmann rearrangement of aromatic and aliphatic carboxamides using (tosylimino)phenyl-λ 3-iodane, PhINTs, as a reagent is reported. Because of the mild reaction conditions, this method is particularly useful for the Hofmann rearrangement of substituted benzamides, which usually afford complex reaction mixtures with other hypervalent iodine oxidants. The mild reaction conditions and high selectivity in the reaction of carboxamides with PhINTs allow the isolation of the initially formed labile isocyanates or their subsequent conversion to stable carbamates by treatment with alcohols.
| Original language | English |
|---|---|
| Pages (from-to) | 2087-2091 |
| Number of pages | 5 |
| Journal | Journal of Organic Chemistry |
| Volume | 77 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 17 Feb 2012 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
(Tosylimino)phenyl-λ 3-iodane as a reagent for the synthesis of methyl carbamates via hofmann rearrangement of aromatic and aliphatic carboxamides. / Yoshimura, Akira; Luedtke, Matthew W.; Zhdankin, Viktor V.
In: Journal of Organic Chemistry, Vol. 77, No. 4, 17.02.2012, p. 2087-2091.Research output: Contribution to journal › Article
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TY - JOUR
T1 - (Tosylimino)phenyl-λ 3-iodane as a reagent for the synthesis of methyl carbamates via hofmann rearrangement of aromatic and aliphatic carboxamides
AU - Yoshimura, Akira
AU - Luedtke, Matthew W.
AU - Zhdankin, Viktor V.
PY - 2012/2/17
Y1 - 2012/2/17
N2 - A new, mild procedure for the Hofmann rearrangement of aromatic and aliphatic carboxamides using (tosylimino)phenyl-λ 3-iodane, PhINTs, as a reagent is reported. Because of the mild reaction conditions, this method is particularly useful for the Hofmann rearrangement of substituted benzamides, which usually afford complex reaction mixtures with other hypervalent iodine oxidants. The mild reaction conditions and high selectivity in the reaction of carboxamides with PhINTs allow the isolation of the initially formed labile isocyanates or their subsequent conversion to stable carbamates by treatment with alcohols.
AB - A new, mild procedure for the Hofmann rearrangement of aromatic and aliphatic carboxamides using (tosylimino)phenyl-λ 3-iodane, PhINTs, as a reagent is reported. Because of the mild reaction conditions, this method is particularly useful for the Hofmann rearrangement of substituted benzamides, which usually afford complex reaction mixtures with other hypervalent iodine oxidants. The mild reaction conditions and high selectivity in the reaction of carboxamides with PhINTs allow the isolation of the initially formed labile isocyanates or their subsequent conversion to stable carbamates by treatment with alcohols.
UR - http://www.scopus.com/inward/record.url?scp=84857200336&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84857200336&partnerID=8YFLogxK
U2 - 10.1021/jo300007c
DO - 10.1021/jo300007c
M3 - Article
VL - 77
SP - 2087
EP - 2091
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 4
ER -