950-15-2

Upstream product

• 119-61-9 benzophenone 
• 75-09-2 dichloromethane 
• 947-91-1 Diphenylacetaldehyde 
• 947-90-0 2,2-diphenyl-vinylamine 
• 593-71-5 Chloroiodomethane 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 1689-71-0 2,3-diphenyloxirane 
• 107116-36-9 Pentachloro<2.2-diphenyl-1-(1-pyridinio)ethoxy>antimonat 

Downstream Products

• 1065-02-7 [N'-(2,4-dinitro-phenyl)-hydrazino]-diphenyl-acetaldehyde-(2,4-dinitro-phenylhydrazone) 
• 983-82-4 (2,4-dinitro-phenyl)-(2,2-diphenyl-vinyl)-diazene 
• 1042684-32-1 C₂₃H₃₁NO₆P₂ 

Relevant academic research and scientific papers

Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes

A straightforward flow synthesis of α-chloro aldehydes has been developed. The strategy involves, for the first time, the thermal unstable chloroiodomethyllithium carbenoid and carbonyl compounds. A batch versus flow comparative study showcases the superb capability of flow technology in prolonging the lifetime of the lithiated carbenoid, even at -20 °C. Remarkably, the high chemoselectivity realized in flow allowed for preparing polyfunctionalized α-chloro aldehydes not easily accessible with traditional batch procedures.

Chemoselective halogenation of 2-hydroperfluoroalkyl aldehydes

2-Hydroaldehydes, RfCH(R)CHO, where Rf = CF 3, C2F5, n-C3F7 and R = CF3, C2F5, n-C3F7, Ph, H, were prepared via acid hydrolysis of the corresponding vinyl ethers, R fC(R) = CHOCH3, which can be readily prepared by reaction of Ph3P+C?HOCH3 with the corresponding ketone. The 2-hydroaldehydes can be chemoselectively converted to the acyl halide, RfCH(R)C(O)X (X = Cl, Br), via free-radical halogenation. The perfluoroalkyl group deactivates the 2-position toward radical abstraction of the 2-hydrogen, and halogenation occurs exclusively at the formyl hydrogen. However, halogenations of the 2-hydroaldehydes in glacial acetic acid chemoselectively gives the 2-haloaldehydes, RfCX(R)CHO, X = Cl, Br. Hydrolysis of the 2-hydroperfluoroacyl halides provides a useful route to 2-hydroperfluoroalkyl branched carboxylic acids, useful ketene precursors. This route avoids the use of toxic fluoroolefins, such as perfluoroisobutylene.

Synthesis of 1,1-bisphosphono-2-aza-1,3-dienes, a new class of electron-deficient azadienes

1,1-Bisphosphono-2-aza-1,3-dienes are formed by 1,4-dehydrohalogenation of the corresponding N-(bisphosphonomethyl)-α-haloimines in moderate to good yields. The precursors could be formed by condensation of bisphosphono-amines and the corresponding α-haloaldehydes.

One-pot conversion of α-substituted arylacetaldehydes into α-dicarbonyl compounds

α-dicarbonyl compounds 7-12 can be easily prepared by reaction of methylene chloride solutions of several α-substituted arylacetaldehydes 1-6 with a slight excess of tris-(o,p-dibromophenyl) ammoniumyl hexachloro antimonate A.

Anomer Controlled Substitution Reactions with Some N-Alkylpyridinium Compounds

The results of semiempirical MNDO calculations on bond lengths, heats of formation, and net atomic charges of compounds 6, 7, and 8, which all contain an N-alkylpyridinium moiety (see Table 1), allow general trends to be recognized.These trends allow the prediction of important reactivity characteristics of this series of compounds and were the reason for the synthesis of compounds 9, 24, and 26 and for tests of their usefulness.Specifically, the C1-N2 bond length serves as a useful criterion for the reactivity with nucleophilic partners, especially in combination with thermodynamic data calculated from reactions (3) and (4) (Tables 3 and 4).In 7 and 8, this bond is very long as a consequence of an extreme anomeric effect.This observation is reflected in the (experimentally tested) property of the complexes 9 to split off the pyridine moiety.The Cl atom in 6a does not influence the C1-N2 bond length but it does activate the C1 atom toward nucleophilic attack and can itself function as the leaving group . - A remarkable example, both on the basis of the MNDO results (using the model compound 6i) and from the experimental viewpoint, was observed for the class of compounds 24a: The calculated C1-N2 bond length of 6i (1.563 Angstroem) could be classified as adequate for nucleophilic substitution of the pyridine moiety controlled by the anomeric effect on the basis of experimental tests.Whereas "normal" N-alkylpyridinium salts (e.g. the N-methylpyridinium cation, 6b) are hardly ever attacked in the C1 position, the preparative usefulness of this structural element can now be considerably increased by use of the anomeric effect.This is demonstrated by the synthesis of compounds 5, 9h, 17, and 22 from 9, 25a and 25b from 24a as well as 27a from 26a.