Welcome to LookChem.com Sign In|Join Free

Article Doi

Synthesis of 1,2-Diazetidinones (Aza-β-lactams) by Photochemical Ring Contraction

DOI: 10.1039/P19870000877

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 877 - 884 (1987)

Update date:2022-08-03

Topics:

Authors:

Lawton, GeoffreyLawton, Geoffrey

Moody, Christopher J.Moody, Christopher J.

Pearson, Christopher J.Pearson, Christopher J.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19870000877

Irradiation of 4-diazopyrazolidine-3,5-diones (11) in the presence of alcohols, diethylamine, or water gives 1,2-diazetidinones (12) formed by photochemical Wolff rearrangement with ring contraction followed by reaction of the resulting ketene with the nucleophile.In the case of the bicyclic diazo compound (11d) a fragmentation reaction competes with ring contraction.The aza-β-lactams (12) show the expected high frequency carbonyl stretch in their i.r. spectra.The acid (12e) readily decarboxylates to give the 4-unsubstituted 1,2-dibenzyldiazetidinone (28), the four-membered ring of which is cleaved by alkaline hydrolysis, lithium aluminium hydride or diborane to give (29), (30), and (31), respectively (Scheme 9).Attempts to modify the carboxy substituent of (12e) into an acylamino group were unsuccessful.

View More

Products guided by the article

Product name:ethyl 1,2-dibenzyl-3-oxo-1,2-diazetidine-4-carboxylate

Cas No:93847-26-8

93847-26-8

R&D Labs maybe for 93847-26-8

Relevant to this article

Hot Product