146767-40-0Relevant academic research and scientific papers
A novel approach to 1-aryl-2-(p-tolylazo)alkenes from alkyl aryl ketones
Caposcialli, Nadia,Dell'Erba, Carlo,Novi, Marino,Petrillo, Giovanni,Tavani, Cinzia
, p. 5315 - 5324 (2007/10/03)
1-Aryl-2-(p-tolylazo)alkenes were synthesized starting from alkyl aryl ketones in good overall yield. The employed three-step procedure involves: i) α-p-tolylhydrazonylation of ketone enolates with tert-butyl p- tolylazosulfide 1; ii) selective reduction of the carbonyl function of the obtained α-p-tolylhydrazono ketones 3 with NaBH4; iii) dehydration of the ensuing hydrazono alcohols 4 either in an Et2O/dil. H2SO4 two-phase system or in pyridine/acetie anhydride.
COMPETITIVE PATHWAYS IN THE REACTION BETWEEN AROMATIC AZOSULFIDES AND ENOLATES IN DMSO
Dell'Erba, Carlo,Novi, Marino,Petrillo, Giovanni,Tavani, Cinzia
, p. 409 - 410 (2007/10/02)
The outcome of the reaction between azosulfides 1 and ketone enolates is influenced by the presence of suitable alkyl substituents on the aryl moiety of 1.The system can thus be conveniently exploited for the selective synthesis of different classes of derivatives of remarkable applicative interest, namely α-aryl ketones, α-arylhydrazono ketones, or indazoles.
α-arylation vs. α-arylhydrazonylation of alkyl aryl ketones with arylazo tert-butyl sulfides
Dell'Erba,Novi,Petrillo,Tavani
, p. 235 - 242 (2007/10/02)
Potassium enolates of alkyl aryl ketones react selectively in DMSO with phenylazo 1a and 4-methylphenylazo tert-butyl sulfide 1b undergoing respectively effective α-phenylation via S(RN)1 and α-(4-methylphenyl)hydrazonylation via elimination-addition.
