826-00-6Relevant academic research and scientific papers
The direct anti-Markovnikov addition of mineral acids to styrenes
Wilger, Dale J.,Grandjean, Jean-Marc M.,Lammert, Taylor R.,Nicewicz, David A.
, p. 720 - 726 (2014/08/05)
The direct anti-Markovnikov addition of strong Bronsted acids to alkenes remains an unsolved problem in synthetic chemistry. Here, we report an efficient organic photoredox catalyst system for the addition of HCl, HF and also phosphoric and sulfonic acids to alkenes, with complete regioselectivity. These transformations were developed using a photoredox catalyst in conjunction with a redox-active hydrogen atom donor. The nucleophile counterion plays a critical role by ensuring high reactivity, with 2,6-lutidinium salts typically furnishing the best results. The nature of the redox-active hydrogen atom donor is also consequential, with 4-methoxythiophenol providing the best reactivity when 2,6-lutidinium salts are used. A novel acridinium sensitizer provides enhanced reactivity within several of the more challenging reaction manifolds. This Article demonstrates how nucleophilic addition reactions mediated by photoredox catalysis can change the way electrophilic and homofugal precursors are constructed.
Synthesis of (+)-ar-Turmerone Employing Organolithium Reagents
Gharpure, M. M.,Joshi, P. L.,Rao, A. S.
, p. 1214 - 1215 (2007/10/02)
Chlorodecarboxylation of (+/-)-β,4-dimethylbenzenepropionic acid (7) with lead tetraacetate and lithium chloride furnishes (+/-)-1-(2-chloro-1-methylethyl)-4-methylbenzene (6).Lithium salt of 3-methyl-2-butenoic acid (11) reacts with 2-(p-tolyl)-n-propyllithium (8) prepared in situ from (+/-)-6 to furnish (+/-)-ar-turmerone (1).Optically active (+)-1 is prepared by reacting lithium salt of the acid (+)-7 with isobutenyllithium.
RELATIONSHIP GOVERNING THE ALKYLATION OF AROMATIC HYDROCARBONS WITH ALLYL CHLORIDE AND BROMIDE IN THE PRESENCE OF SULFURIC ACID
Magerramov, M. N.
, p. 1485 - 1488 (2007/10/02)
The kinetic relationships governing the alkylation of aromatic hydrocarbons by allyl chloride and allyl bromide in the presence of sulfuric acid were studied.It was established that the reactivity of the aromatic hydrocarbons varies in relation to the "activity" of the allyl halides in the order allyl chloride > allyl bromide > propylene.
