Diazirines in carbenoid reactions catalyzed by rhodium(II) carboxylates
β Scribed by Michael P. Doyle; Kenneth G. High; Su-Min Oon; Antonio K. Osborn
- Book ID
- 104229551
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 271 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Diazo compounds formed by thermal or photolytic rearrangement of 3-alkyl-3-phenyldiazirines in the presence of catalytic amounts of rhodium(ll) perfluorobutyrate are effectively directed to metal carbenoid products with minimal competition from processes which are dominant when the diazo compound is used directly or when the diazirine is decomposed in the absence of the catalyst.
π SIMILAR VOLUMES
Rhodium(k) acetate and rhodium(h) acetamide catalyzed decomposition of diazo esters forms "I-lactones in high yield and with exceptionally high regio-and diastereoselectivity.
A simple one-pot procedure is described for the preparation of spiro [4,4]nonane-2,7-dione derivatives from open chain bis(oc-diazoketones). The reactions proceed by an intramolecular Rh(II)carbenoid insertion into a methylene C-H bond yielding a cyclopentane which subsequently undergoes C-H methine
Rhodium has proven to be an extremely useful metal due to its ability to catalyze an array of synthetic transformations, with quite often-unique selectivity. Hydrogenation, C-H activation, allylic substitution, and numerous other reactions are catalyzed by this metal, which presumably accounts for t