A novel, general method for the synthesis of nitrile oxides: Dehydration of O-silylated hydroxamic acids

Organic Letters

Volumn 2, Issue 4, 2000, Pages 539-541

  Muri, Dieter ^a   Bode, Jeffrey W ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001687772     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991396q     Document Type: Article

References (25)

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15. (a) To our knowledge, there has been only one report of a similar transformation, namely, the thermolysis of 1,3,2,4-dioxathiazole 2-oxides to give apparent generation of nitrile oxides, albeit with competing isocyanate formation. In contrast, cyclic hydroxamate esters give exclusively isocynates via Lossen rearrangement; see: Frantz, J. E.; Pearl, H. K. J. Org. Chem. 1975, 41, 1296.
16. (b) O-Trimethylsilyl hydroximinoyl chlorides have been used to prepare nitrile oxides. However, the necessary intermediates must be prepared from nitrile oxides themselves, and the method is therefore not, in itself, a preparative method for nitrile oxides. Cunico, R. F.; Bedell, L. J. Org. Chem. 1983, 48, 2780.
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21. In preliminary work, we have documented that 3a, 6-dihydro-3H-cyclopenta[c]isoxazoline can be prepared by intramolecular nitrile oxide cycloaddition reaction of the corresponding silylated hydroxamic acid. This result along with an accompanying study of intramolecular cycloadditions utilizing the method described herein is part of ongoing investigations in our group and will be reported as results become available.
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