Spectroscopic detection of an arylchlorocarbene-ethyl acetate carbonyl ylide and subsequent oxirane formation

JE Chateauneuf, MTH Liu

Index: Chateauneuf, John E.; Liu, Michael T. H. Journal of the American Chemical Society, 1991 , vol. 113, # 17 p. 6585 - 6588

Full Text: HTML

Citation Number: 21

Abstract

Abstract: Laser flash photolysis of 3-chloro-3-@-nitrophenyl) diazirine (1) generates the corresponding ground-state singlet carbene (Am,= 310 nm), which reacts with ethyl acetate to form a carbonyl ylide of the ester (A,= 490 nm). The absolute rate constant for ylide formation in CH2CI2 is k=(2.85 f 0.17) X lo6 MI sl. Subsequent cyclization of the ylide to the corresponding oxirane (A,= 350 nm) occurs with a rate constant of 1.26 X lo6 sI (21" C) in ...

Related Articles:

Phosphorus (V)-catalyzed deoxydichlorination reactions of aldehydes

[An, Jie; Tang, Xiaoping; Moore, Joshua; Lewis, William; Denton, Ross M. Tetrahedron, 2013 , vol. 69, # 41 p. 8769 - 8776]

Reactions of organic anions. 161. Dihalomethylation of nitroarenes via vicarious nucleophilic substitution of hydrogen with trihalomethyl carbanions

[Makosza, M.; Owczarczyk, Z. Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5094 - 5100]

Chlorination of oximes. I. Reaction and mechanism of the chlorination of oximes in commercial chloroform and methylene chloride

[Chiang,Y.H. Journal of Organic Chemistry, 1971 , vol. 36, p. 2146 - 2155]

Behavior of carbonyl ylide generated from 3-chloro-3-(p-nitrophenyl) diazirine and acetone. 1, 3-Dipolar cycloaddition to benzaldehyde and epoxide formation

[Ibata, Toshikazu; Toyoda, Jiro; Liu, Michael T. H. Chemistry Letters, 1987 , p. 2135 - 2138]

Chemo-and stereoselectivity of the reaction of aromatic aldehydes with triphenylphosphine and trichloroacetic acid derivatives

[Matveeva; Erin; Osetrov; Leshcheva; Kurts Russian Journal of Organic Chemistry, 2006 , vol. 42, # 3 p. 388 - 392]

More Articles...