19522-37-3

Upstream product

• 79559-51-6 α-bromo-cis-cinnamic acid amide 
• 24247-46-9 α-bromo-cinnamaldehyde-oxime 
• 24247-46-9 α-bromo-cis-cinnamaldehyde seqtrans-oxime 
• 108-24-7 acetic anhydride 
• 19521-13-2 α,β-dibromo-β-phenylpropionitrile 
• 19521-13-2 (+/-)-2r_F,3c_F-dibromo-3cat_F-phenyl-propionitrile 
• 99686-39-2 (E)-2-bromo-3-phenylprop-2-enal 
• 1885-38-7 cinnamic nitrile 
• 859217-21-3 1,2-dimethyl-1H-indazol-2-ium-3-carboxylate 

Downstream Products

• 15813-24-8 (Z)-2-bromo-3-phenylacrylic acid 
• 872276-59-0 β-ethoxy-cinnamonitrile 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 

Relevant academic research and scientific papers

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

N-heterocyclic carbenes of indazole: Ring enlargement reactions by α-halo ketones and dehalogenations of vicinal dihalides

On decarboxylation, 1,2-dimethylindazolium-3-carboxylate forms the N-heterocyclic carbene, 1,2-dimethylindazol-3-ylidene, which deprotonates α-halo ketones. The resulting indazolium salt and the corresponding enolate form 1:1 adducts which undergo a ring enlargement to cinnolines. Reaction with 2-bromo-2,3-dihydro-1H-inden-1-one gives a 4- hydroxyspiro[cinnoline-3,2′-inden]-1′-one by ring enlargement reaction (X-ray crystal structure analysis). Vicinal dibromides undergo debromination under these conditions to give alkenes, and substrates with 1,2-dibromoethene partial structure give acetylenes. As 3-bromoindazole is found as the second product of this reaction, an E1cb mechanism, initiated by Br+ abstraction by the N-heterocyclic carbene of indazole, is suggested. Georg Thieme Verlag Stuttgart.

Photochemical generation and structure of vinyl radicals

Photolysis of a series of E or Z stereoisomeric α-R-substituted bromostyrenes (R = CH3, F or CN) in methanol yields E and/ or Z stereoisomeric styrenes, which stem from the corresponding vinyl radicals. The results show that the α-Me vinyl radical is a rapidly equilibrating, bent structure, while the α-F vinyl radical is a stable bent species, in agreement with earlier thermal results. The α-CN vinyl radical is assigned as a rapidly inverting bent and not a linear species from the stereochemical results as a function of temperature. Stereochemical data for the α-C(H)=O system in diethyl ether indicate a stable bent vinyl radical as product forming species. The conclusions are supported by quantum chemical computations. Wiley-VCH Verlag GmbH & Co. KGaA.