Rearrangement of 2-Bromo-1-(bromomethyl)ethyl Esters Under Basic Conditions: Scope and Mechanism

Julien Alliot; Edmond Gravel; Eric Doris

doi:10.1055/s-0033-1339649

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(20): 2861-2866
DOI: 10.1055/s-0033-1339649

paper

Rearrangement of 2-Bromo-1-(bromomethyl)ethyl Esters Under Basic Conditions: Scope and Mechanism

Julien Alliot

CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette, France Fax: +33(0)169087991 eMail: eric.doris@cea.fr

,

Edmond Gravel

CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette, France Fax: +33(0)169087991 eMail: eric.doris@cea.fr

,

Eric Doris*

CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette, France Fax: +33(0)169087991 eMail: eric.doris@cea.fr

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Abstract

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Abstract

A novel rearrangement of 2-bromo-1-(bromomethyl)ethyl esters into the corresponding 2-oxopropyl derivatives is reported. The mechanism of this transformation was studied by means of ¹⁸O- and ²H-labeling experiments. The reaction proceeds through a transient dioxolane intermediate that is hydrolyzed to form the corresponding 2-oxopropyl acetate.

Key words

esters - halogens - ketones - rearrangements

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Referenzen

References

1a Hardouin C, Doris E, Rousseau B, Mioskowski C, Nierlich M. Acta Crystallogr., Sect. C 2000; 56: 225
1b Hardouin C, Doris E, Rousseau B, Mioskowski C. Org. Lett. 2002; 4: 1151
1c Hardouin C, Doris E, Rousseau B, Mioskowski C. J. Org. Chem. 2002; 67: 6571
1d Hardouin C, Burgaud L, Valleix A, Doris E. Tetrahedron Lett. 2003; 43: 435
1e Moisan L, Doris E, Rousseau B, Thuéry P. Acta Crystallogr., Sect. C 2004; 60: o792
1f Moisan L, Thuéry P, Nicolas M, Doris E, Rousseau B. Angew. Chem. Int. Ed. 2006; 45: 5334
1g Doris E. Angew. Chem. Int. Ed. 2009; 48: 7480
1h Leroux S, Larquetoux L, Nicolas M, Doris E. Org. Lett. 2011; 13: 3549
1i Giovanelli E, Leroux S, Moisan L, Carreyre H, Thuéry P, Buisson DA, Meddour A, Coustard JM, Thibaudeau S, Rousseau B, Nicolas M, Hellier P, Doris E. Org. Lett. 2011; 13: 4116
1j Giovanelli E, Moisan L, Leroux S, Comesse S, Rousseau B, Hellier P, Nicolas M, Doris E. Chem. Eur. J. 2013; 19: 1170
1k Giovanelli E, Moisan L, Comesse S, Leroux S, Rousseau B, Hellier P, Nicolas M, Doris E. Org. Biomol. Chem. 2013; 11: 5885

2 Alliot J, Gravel E, Pillon F, Buisson DA, Nicolas M, Doris E. Chem. Commun. 2012; 48: 8111
3 Shimizu M, Yoshioka H. J. Chem. Soc., Chem. Commun. 1987; 689
4 Ter-Gabriélyan EG, Avetisyan EA, Gambaryan NP. Russ. Chem. Bull. 1973; 22: 2496

For an example, see:

5a Jung ME, Chu HV. Tetrahedron Lett. 2011; 52: 4512
5b Fichna J, Lewellyn K, Yan F, Roth BL, Zjawiony JK. Bioorg. Med. Chem. Lett. 2011; 21: 160
5c Yajima A, Kagohara Y, Shikai K, Katsuta R, Nukada T. Tetrahedron 2012; 68: 1729

For examples, see:

6a Trukhin DV, Bagryanskaya IY, Gatilov YV, Mikhalina TV, Rogozhnikova OY, Troitskaya TI, Tormyshev VM. Synlett 2005; 2072
6b Su S, Seiple IB, Young IS, Baran PS. J. Am. Chem. Soc. 2008; 130: 16490
6c Altuna-Urquijo M, Gehre A, Stanforth SP, Tarbit B. Tetrahedron 2009; 65: 975

7a Nikishin G, Sokova L, Kapustina N. Russ. Chem. Bull. 2010; 391
7b Parvez M, Kabir SM. H, Sorensen TS, Sun F, Watson B. Can. J. Chem. 2002; 413
7c Föhlisch B, Gottstein W. Liebigs Ann. Chem. 1979; 1768

8 Nakano K, Kodama S, Permana Y, Nozaki K. Chem. Commun. 2009; 6970
9 Salunkhe MM, Sande AR, Kanade AS, Wadgaonkarb ZP. Synth. Commun. 1997; 27: 2885

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