Details
| Original language | English |
|---|---|
| Pages (from-to) | 8242-8250 |
| Number of pages | 9 |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue number | 15 |
| Early online date | 19 Jul 2017 |
| Publication status | Published - 4 Aug 2017 |
| Externally published | Yes |
Abstract
The degradation of geminal diazides is described. We show that diazido acetates are converted into tetrazoles through the treatment with bases. The reaction of dichloro ketones with azide anions provides acyl azides, through in situ formation of diazido ketones. We present experimental and theoretical evidence that both fragmentations may involve the generation of acyl cyanide intermediates. The controlled degradation of terminal alkynes into amides (by loss of one carbon) or ureas (by loss of two carbons) is also shown.
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Journal of Organic Chemistry, Vol. 82, No. 15, 04.08.2017, p. 8242-8250.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Pathways in the Degradation of Geminal Diazides
AU - Holzschneider, Kristina
AU - Häring, Andreas P.
AU - Haack, Alexander
AU - Corey, Daniel J.
AU - Benter, Thorsten
AU - Kirsch, Stefan F.
PY - 2017/8/4
Y1 - 2017/8/4
N2 - The degradation of geminal diazides is described. We show that diazido acetates are converted into tetrazoles through the treatment with bases. The reaction of dichloro ketones with azide anions provides acyl azides, through in situ formation of diazido ketones. We present experimental and theoretical evidence that both fragmentations may involve the generation of acyl cyanide intermediates. The controlled degradation of terminal alkynes into amides (by loss of one carbon) or ureas (by loss of two carbons) is also shown.
AB - The degradation of geminal diazides is described. We show that diazido acetates are converted into tetrazoles through the treatment with bases. The reaction of dichloro ketones with azide anions provides acyl azides, through in situ formation of diazido ketones. We present experimental and theoretical evidence that both fragmentations may involve the generation of acyl cyanide intermediates. The controlled degradation of terminal alkynes into amides (by loss of one carbon) or ureas (by loss of two carbons) is also shown.
UR - http://www.scopus.com/inward/record.url?scp=85027043031&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b01019
DO - 10.1021/acs.joc.7b01019
M3 - Article
C2 - 28722411
AN - SCOPUS:85027043031
VL - 82
SP - 8242
EP - 8250
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 15
ER -