97879-05-5Relevant academic research and scientific papers
Iron(II) vinylidenes and chromium carbene complexes in β-lactam synthesis
Barrett, Anthony G. M.,Mortier, Jacques,Sabat, Michal,Sturgess, Michael A.
, p. 2553 - 2561 (2008/10/08)
Reaction of the chromium carbene 7 with toluene-4-sulfonyl chloride and the imine 8a gave 9a (26%). Alternatively reactions of the cationic iron(II) vinylidene reagents 20a,b, and 23a-d with the imines 8a-d and 2-thiazolines 28a-c gave the corresponding azetidinylidene complexes 21a,b, 24a-f, and 29a-d (11-82%). Subsequent oxidation of these complexes using iodosobenzene, pyridine N-oxide, bromine, air, or tetrabutylammonium nitrite gave the monocyclic or bicyclic β-lactams 10a-c, 25a-d, and 30a-c (8-97%).
Application of pentacarbonylchromium carbenes in β-lactam synthesis: Preparation and X-ray crystallographic study of ( 1-methyl-4-phenyl-3(E )-( phenylmethylene )-azetidinylidene)pentacarbonylchromium
Barrett, Anthony G. M.,Brock, Carolyn P.,Sturgess, Michael A.
, p. 1903 - 1905 (2008/10/08)
The reaction of the tetramethylammonium salt of (1-hydroxyethylidene)pentacarbonylchromium (1c) with toluene-4-sulfonyl chloride and N-benzylidenemethylamine (7a) gave the title azetidine complex 8a (25%), whose structure was confirmed by a crystal structure determination. Subsequent oxidation with pyridine N-oxide gave 1-methyl-4-(phenylmethylene)-2-azetidinone 9a (96%). These reactions were extended to N-(3-methylbenzylidene)methylamine and N-(4-methylbenzylidene)-methylamine.
