The reaction of alkenes with AgNO2/TMSCl: The synthesis of 1,2,5-oxadiazole-2-oxides (Furoxans) via nitroso nitrates

Date

2005-11-01

Author

Demir, Ayhan Sıtkı
Findik, H

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

107
views

0
downloads

The reaction of AgNO2/TMSCl with olefins affords nitrosonitrate, which arc converted into (alpha-nitroximes in good yield. Both nitrosonitrate and nitroximes are converted with acids into furoxane in high yield. The reaction of AgNO2 with TMSCl furnished first N2O3 and hexamethylsiloxane. The nitroso nitrates are obtained by addition of N2O3 to the olefines.

Subject Keywords

Organic Chemistry, Biochemistry

URI

https://hdl.handle.net/11511/51016

Journal

LETTERS IN ORGANIC CHEMISTRY

DOI

https://doi.org/10.2174/157017805774296948

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Unusual fragmentation of fulvene endoperoxides with phenyliodosyl bis(trifluoroacetate) (PIFA) Ozer, G; Saracoglu, N; Balcı, Metin (Wiley, 2003-05-01) Reaction of unsaturated fulvene endoperoxides with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate gave saturated fulvene endoperoxides containing the 1,2-dihydropyridazine ring. Treatment of dihydropyridazine endoperoxides with water followed by phenyliodosyl bis(trifluoroacetate) oxidation provided acrylic acid derivatives and dimethyl pyridazine-3,6-dicarboxylate.
Synthesis and chemistry of unusual bicyclic endoperoxides containing the pyridazine ring Ozer, G; Saracoglu, N; Balcı, Metin (American Chemical Society (ACS), 2003-09-05) Inverse-Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with unsaturated bicyclic endoperoxides gave the bicyclic endoperoxides containing the pyridazine ring. The NEt3 and CoTPP (TPP = tetraphenylporphyrin) catalyzed reaction of endoperoxide 8 resulted in the formation of hydroxy ketone 11 and cis-diol 9. Cleavage of the peroxide linkage in 8 with thiourea provided cis-diol 9. Oxidation of hydroxy ketone 11 and cis-diol 9 led to the phthalazine-5,8-dione 10. Furthermore, the various tr...
A facile synthesis of various butenolides Tanyeli, Cihangir (Informa UK Limited, 2000-01-01) The synthesis of alpha'-acyloxy-alpha,beta-unsaturated cyclic ketones from the corresponding alpha,beta-unsaturated cyclic ketones by using manganese (III) acetate in combination with 2-chloropropionic acid followed by subsequent Arbuzov and intramolecular Horner-Emmons cyclization reactions provided a convenient synthetic pathway to various butenolides 4a-d.
THE MILD N-NITROSATION OF SECONDARY-AMINES WITH TRICHLORONITROMETHANE Demir, Ayhan Sıtkı; MAHASNEH, AS; AKSOY, H; GERCEK, Z (Informa UK Limited, 1992-01-01) Reaction of trichloronitromethane with secondary amine leads to the formation
Synthesis of various camphor-based chiral pyridine derivatives Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19) (+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.

Citation Formats

A. S. Demir and H. Findik, “The reaction of alkenes with AgNO2/TMSCl: The synthesis of 1,2,5-oxadiazole-2-oxides (Furoxans) via nitroso nitrates,” LETTERS IN ORGANIC CHEMISTRY, pp. 602–604, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51016.