111322-83-9

Basic information

• Product Name: (1S,2S)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester
• CAS NO: 111322-83-9
• Molecular Weight: 341.748
• Mol File: 111322-83-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,2S)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester(111322-83-9)
• EPA Substance Registry System: (1S,2S)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester(111322-83-9)

Safety Data

• Hazardous Substances Data: 111322-83-9(Hazardous Substances Data)

Upstream product

• 67-64-1 acetone 
• 623-91-6 diethyl Fumarate 
• 39184-67-3 3-chloro-3-(p-nitrophenyl)diazirine 
• 141-78-6 ethyl acetate 
• 102146-13-4 (p-nitrophenyl)chlorocarbene 
• 141-05-9 Diethyl maleate 

Relevant articles and documents

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

Laser flash photolysis of 3-chloro-3-(p-nitrophenyl)diazirine (1) generates the corresponding ground-state singlet carbene (λmax = 310 nm), which reacts with ethyl acetate to form a carbonyl ylide of the ester (λmax = 490 nm). The absolute rate constant for ylide formation in CH2Cl2 is k = (2.85 ± 0.17) × 106 M-1 s-1. Subsequent cyclization of the ylide to the corresponding oxirane (λmax = 350 nm) occurs with a rate constant of 1.26 × 106 s-1 (21 °C) in ethyl acetate with Arrhenius activation parameters for oxirane formation of Eact = 6.68 ± 0.19 kcal/mol and log A (s-1) = 11.08 ± 0.15. The carbonyl ylide is also intercepted with the dipdarophile, diethyl fumarate, with a rate constant of (1.04 ± 0.07) × 107 M-1 s-1. Additionally, solvent polarity effects on (p-nitrophenyl)chlorocarbene reactivity and spectroscopic evidence of oxirane formation (λmax = 350 nm) from the related acetone ylide of (p-nitrophenyl)chlorocarbene are presented.

FORMATION OF A DIPOLAR ADDUCT IN THE REACTION OF ARYLCHLOROCARBENES WITH DIETHYL MALEATE

Non-concerted addition of arylchlorocarbenes to diethyl maleate, accompanied by isomerization of maleate to fumarate, is consistent with an intermediate carbene-alkene dipolar adduct.