14688-37-0

Basic information

• Product Name: cis-p,p'-dinitrostilbene oxide
• Synonyms: cis-p,p'-dinitrostilbene oxide
• CAS NO: 14688-37-0
• Molecular Weight: 286.244
• Mol File: 14688-37-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: cis-p,p'-dinitrostilbene oxide(CAS DataBase Reference)
• NIST Chemistry Reference: cis-p,p'-dinitrostilbene oxide(14688-37-0)
• EPA Substance Registry System: cis-p,p'-dinitrostilbene oxide(14688-37-0)

Safety Data

• Hazardous Substances Data: 14688-37-0(Hazardous Substances Data)

Upstream product

• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 555-16-8 4-nitrobenzaldehdye 
• 619-93-2 (Z)-4,4'-dinitrostilbene 
• 100-14-1 4-nitrobenzyl chloride 
• 83294-14-8 lithium 2,4-dimethyl-3-nitropentan-3-ide 
• 3145-86-6 4-nitrobenzyl iodide 

Downstream Products

• 13295-04-0 1.2-bis(4-nitrophenyl)ethane-1,2-diol 
• 57507-60-5 2-Methoxy-1,2-bis-(4-nitro-phenyl)-ethanone 
• 736-31-2 trans-4,4'-dinitrostilbene 
• 1033-26-7 4,4'-dinitrobenzophenone 
• 6067-45-4 4,4'-dinitrobenzil 
• 873420-19-0 α'-iodo-4,4'-dinitro-bibenzyl-α-ol 
• 619-93-2 4,4'-dinitro stilbene 
• 57507-54-7 (1S,2R)-2-Methoxy-1,2-bis-(4-nitro-phenyl)-ethanol 
• 36898-62-1 4,4'-dinitrobenzoin 
• 555-16-8 4-nitrobenzaldehdye 
• 105222-70-6 α,α'-dichloro-4,4'-dinitro-bibenzyl 
• 968-01-4 (2SR,3SR)-2,3-bis(4-nitrophenyl)oxirane 

Relevant articles and documents

Synthesis of Epoxides from Alkyl Bromides and Alcohols with in Situ Generation of Dimethyl Sulfonium Ylide in DMSO Oxidations

Direct conversion of the readily available alkyl bromides and alcohols to value-added epoxides using dimethyl sulfoxide (DMSO) under mild reaction conditions has been developed. Benzyl and allyl bromides, and activated and unactivated alcohols all proceeded smoothly to give epoxides in high to excellent yield. Dimethyl sulfide, generated by DMSO oxidations, was in situ elaborated to form the substituted dimethyl sulfonium ylide species that participates in the Corey-Chaykovsky epoxidation in a domino and one-pot fashion, respectively.

Experimental evidence for multiple oxidation pathways in the (salen)Mn-catalyzed epoxidation of alkenes

The substrate electronic effects on the selectivity in the catalytic epoxidation of para-substituted cis stilbenes 2a-i were investigated by using (R,R)-[N,N′-bis(3,5-di-tBu-salicylidene)-1,2-cyclohexanediamine] manganese(III) chloride 1 in benzene as the catalyst with iodosobenzene as the terminal oxidant. A Hammett study of the selectivity results reveals a stronger electrophilic character than previously assumed in the (salen)Mn-catalyzed reaction. In general, the best correlations with the experimental values were obtained by using the Hammett σ+ values, which gave ρ = -1.37 for the rate of cisepoxide formation and ρ = -0.43 for the rate of the stepwise process leading to the corresponding trans product. The reaction involves two separate pathways as indicated also by the competitive breakdown of the intermediate on the path to trans epoxide for methoxy-substituted substrates. The asynchronicity in the concerted pathway leading to cis epoxide is apparent for 4-methoxy-4′-nitrostilbene, which yields cis epoxide with 75% ee entirely as a result of electronic effects.

Preparation of optically active stilbene oxides via sulfonium salts derived from C2 symmetric thiolanes

Trans-stilbene oxides have been obtained in up to 83% enantiomeric excess via reaction of S-benzyl ylides prepared from optically active trans-2,5-disubstituted thiolanes.