Search for dioxocarbenes in photochemical reactions of 5-diazo-4,6-dioxo-1, 3-dioxanes, associated diazirines, and S-ylides

Tetrahedron Letters

Volumn 46, Issue 3, 2005, Pages 435-438

  Shevchenko, V V ^a   Khimich, N N ^a   Platz, M S ^b   Nikolaev, V A ^a  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

Carbenes; Diazirines; Diazo compounds; Photochemistry; Sulfonium ylides

Indexed keywords

AZIRINE DERIVATIVE; CARBENE; DIMETHYL SULFIDE; DIOXANE DERIVATIVE; METHANOL; PYRIDINE; SULFONIUM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 11144292112     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.102     Document Type: Article

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25. 13C NMR, and mass spectra. All new compounds were characterized and gave satisfactory spectral data
26. 2O/petroleum, then pure EtOH) to give the products: diazirine 3b, 456 mg (43%); methyl esters 7b, 200 mg (19%, ratio of stereoisomers ∼ 1/1.5); diazodioxodioxane 2b, 200 mg (19%); sulfonium ylide 4b, 21 mg (2%)
27. 1H spectra of individual compounds, obtained in the course of preparative photolysis of diazo compounds 2a,b
28. 5a,5c (> 95%) and traces of dioxane 7
29. 3)