detrifluoroacetylative diazo group transfer: (E)-1-Diazo-4-Phenyl-3-Buten-2-One: [3-Buten-2-one, 1-diazo-4-phenyl-]

Organic Syntheses

Volumn 73, Issue , 1996, Pages 134-

  Danheiser, Rick L ^b   Miller, Raymond F ^b   Brisbois, Ronald G ^a   Clark, Cameron ^b   Martin, Stephen F ^b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85026877531     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.073.0134     Document Type: Article

References (26)

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4. Lowe, G.; Ramsay, M. V. J. Chem. Soc., Perkin Trans. I 1973, 479;
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6. For reviews of methods for the synthesis of Į-diazo ketones, see (a) Regitz, M.; Maas, G. "Diazo Compounds: Properties and Synthesis"; Academic Press: New York; 1986;
7. Regitz, M. In "The Chemistry of Diazonium and Diazo Groups"; Patai, S., Ed.; Wiley: New York, 1978; Part 2, Chapter 17, pp. 751–820.
8. For reviews of diazo group transfer, see (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1967, 6, 733;
9. Regitz, M. Synthesis 1972, 351;
10. Recent methods for diazo group transfer include: (a) Koskinen, A. M. P.; Munoz, L. J. Chem. Soc., Chem. Commun. 1990, 652;
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12. Popic, V. V.; Korneev, S. M.; Nikolaev, V. A.; Korobitsyna, I. K. Synthesis 1991, 195.
13. Diazo transfer from 2,4,6-triisopropylphenylsulfonyl azide to the enolate derivatives of hindered cyclic ketones can be achieved by using phase transfer conditions: Lombardo, L.; Mander, L. N. Synthesis 1980, 368.
14. Evans and co-workers have reported successful diazo transfer from p-nitrobenzenesulfonyl azide (PNBSA) to the enolate derivatives of an N-acyloxazolidinone and a benzyl ester: (a) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. However, we have not been able to achieve efficient diazo transfer to ketone enolates employing these conditions. For example, exposure of the lithium enolate of acetophenone to 1.2 equiv of PNBSA in THF at í78°C for 15 min gave Į-diazoacetophenone in only 21% yield.
15. Regitz, M.; Menz, F. Chem. Ber. 1968, 101, 2622;
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