Baker-Ollis sydnone synthesis

The Baker-Ollis sydnone synthesis is a name reaction in organic chemistry for the synthesis of sydnones . John Campbell Earl (1890–1978) and Alan W. Mackney (1913–2003) reported for the first time in 1935 on the synthesis, which was later named after Wilson Baker (1900–2002) and William David Ollis (1924–1999) - the Researchers who suggested the structure of the sydnon.

Overview reaction

Sydnone is synthesized from N -substituted α-amino acids and a dehydrating compound such as acetic anhydride .

The structure of the sydnone shown in the overview reaction is, according to Baker and Ollis, a particularly relevant boundary structure. For the Sydnon can u. a. draw the following mesomeric boundary structures :

Reaction mechanism

In the proposed reaction mechanism, the N -substituted α-amino acids first attack acetic anhydride nucleophilically. After double elimination of acetic acid and cyclization, the sydnone is then formed.

modification

In addition to acetic anhydride, trifluoroacetic anhydride , thionyl chloride and phosgene can also be used as the dehydrating compound. If trifluoroacetic anhydride is used, the reaction can take place particularly quickly. N, N -diisopropylcarbodiimide can also be used in aqueous solutions at room temperature.

Individual evidence

↑ ^a ^b ^c ^d Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , doi : 10.1002 / 9780470638859 .
^ DJ Brown: Earl, John Campbell (1890-1978) . In: Australian Dictionary of Biography . National Center of Biography, Australian National University, Canberra ( edu.au [accessed May 26, 2019]).
↑ Mackney, Alan W. (OBE) (1913-) - People and organizations. Retrieved May 26, 2019 .
↑ J. Campbell Earl, Alan W. Mackney: 204. The action of acetic anhydride on N-nitrosophenylglycine and some of its derivatives . In: Journal of the Chemical Society (Resumed) . 1935, p. 899 , doi : 10.1039 / jr9350000899 .
↑ McOmie JFW, Lloyd DMG: Wilson Baker. 24 January 1900 - 3 June 2002 . In: Biographical Memoirs of Fellows of the Royal Society . tape 49 , December 1, 2003, p. 15-38 , doi : 10.1098 / rsbm.2003.0002 .
^ Blackburn GM, Sutherland IO: William David Ollis. 22 December 1924 - 13 June 1999 . In: Biographical Memoirs of Fellows of the Royal Society . tape 47 , November 1, 2001, p. 395-413 , doi : 10.1098 / rsbm.2001.0023 .
^ ^A ^b Wilson Baker, WD Ollis: Meso-ionic compounds . In: Quarterly Reviews, Chemical Society . tape 11 , no. 1 , 1957, pp. 15 , doi : 10.1039 / qr9571100015 .
^ Wilson Baker, WD Ollis, VD Poole: 320. Cyclic meso-ionic compounds. Part III. Further properties of the sydnones and the mechanism of their formation . In: Journal of the Chemical Society (Resumed) . 1950, p. 1542 , doi : 10.1039 / jr9500001542 .

[:0-1] Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , doi : 10.1002 / 9780470638859 .

[2] DJ Brown: Earl, John Campbell (1890-1978) . In: Australian Dictionary of Biography . National Center of Biography, Australian National University, Canberra ( edu.au [accessed May 26, 2019]).

[3] Mackney, Alan W. (OBE) (1913-) - People and organizations. Retrieved May 26, 2019 .

[4] J. Campbell Earl, Alan W. Mackney: 204. The action of acetic anhydride on N-nitrosophenylglycine and some of its derivatives . In: Journal of the Chemical Society (Resumed) . 1935, p. 899 , doi : 10.1039 / jr9350000899 .

[5] McOmie JFW, Lloyd DMG: Wilson Baker. 24 January 1900 - 3 June 2002 . In: Biographical Memoirs of Fellows of the Royal Society . tape 49 , December 1, 2003, p. 15-38 , doi : 10.1098 / rsbm.2003.0002 .

[6] Blackburn GM, Sutherland IO: William David Ollis. 22 December 1924 - 13 June 1999 . In: Biographical Memoirs of Fellows of the Royal Society . tape 47 , November 1, 2001, p. 395-413 , doi : 10.1098 / rsbm.2001.0023 .

[:1-7] A ^b Wilson Baker, WD Ollis: Meso-ionic compounds . In: Quarterly Reviews, Chemical Society . tape 11 , no. 1 , 1957, pp. 15 , doi : 10.1039 / qr9571100015 .

[8] Wilson Baker, WD Ollis, VD Poole: 320. Cyclic meso-ionic compounds. Part III. Further properties of the sydnones and the mechanism of their formation . In: Journal of the Chemical Society (Resumed) . 1950, p. 1542 , doi : 10.1039 / jr9500001542 .