104-82-5Relevant articles and documents
A novel synthesis of tolunitriles by selective ammoxidation
Xie, Guangyong,Zhang, Aiqing,Huang, Chi
, p. 969 - 973 (2010)
A new approach to synthesize tolunitriles is reported. Tolunitriles can be prepared by selective ammoxidation of methylbenzyl chlorides prepared by chloromethylation of toluene. The total yields can reach 83% and the selectivity of tolunitriles is almost 100%. This approach provides a new path for preparing alkylbenzonitriles and other aromatic nitriles.
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Dalrymple et al.
, p. 2647 (1964)
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Shiner et al.
, p. 4838,4840 (1969)
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Regiospecific chlorination of xylenes using K-10 montmorrillonite clay
Thirumamagal,Narayanasamy, Sureshbabu,Venkatesan
, p. 2820 - 2825 (2008)
Regiospecific chlorination of xylenes has been developed by employing NCS as a reagent and K-10 montmorrillonite clay as a solid support. Copyright Taylor & Francis Group, LLC.
Photocatalytic activation of N-chloro compounds for the chlorination of arenes
Hering, Thea,K?nig, Burkhard
, p. 7821 - 7825 (2016)
Photoredox catalysis activates N-chloramines and N-chloro-succinimide (NCS) for the electrophilic chlorination of arenes. The photooxidation of the nitrogen atom to a radical cation induces a positive polarization on the chlorine atom, which results in a higher reactivity in electrophilic aromatic chlorination reactions.
Mechanism of solvolysis of substituted benzyl chlorides in aqueous ethanol
Denegri, Bernard,Mati?, Mirela,Va?ko, Monika
supporting information, (2021/11/22)
The mechanism of solvolyses of activated ortho-, meta- and para-substituted benzyl chlorides in aqueous ethanol has been studied by using the Hammett-Brown and Yukawa-Tsuno treatments as well as by correlating logarithms of solvolysis rate constants with relative stabilities of corresponding benzyl carbocations in water calculated at the IEFPCM-M06–2X/6-311+G(3df,3pd) level of theory. Benzyl chlorides containing strong conjugative electron-donors in the para-position solvolyze by the SN1 mechanism, whereas other activated benzyl chlorides solvolyze by the SN2 mechanism via loose transition states.
Nickel catalyzed deoxygenative cross-coupling of benzyl alcohols with aryl-bromides
Kumar Chenniappan, Vinoth,Peck, Devin,Rahaim, Ronald
, (2020/03/03)
A nickel-catalyzed cross-electrophile coupling of benzyl alcohols with aromatic bromides has been developed. This deoxygenative cross-coupling occurs under mild reaction conditions at ambient temperature affording diarylmethanes, or 1,3-diarylpropenes from benzyl allyl alcohols. The system demonstrated good chemoselectivity tolerating an assortment of reactive functional groups.
α-Diimine-Niobium Complex-Catalyzed Deoxychlorination of Benzyl Ethers with Silicon Tetrachloride
Parker, Bernard F.,Hosoya, Hiromu,Arnold, John,Tsurugi, Hayato,Mashima, Kazushi
supporting information, p. 12825 - 12831 (2019/10/19)
α-Diimine niobium complexes serve as catalysts for deoxygenation of benzyl ethers by silicon tetrachloride (SiCl4) to cleanly give two equivalents of the corresponding benzyl chlorides, where SiCl4 has the dual function of oxygen scavenger and chloride source with the formation of a silyl ether or silica as the only byproduct. The reaction mechanism has two successive trans-etherification steps that are mediated by the niobium catalyst, first forming one equivalent of benzyl chloride along with the corresponding silyl ether intermediate that undergoes the same reaction pathway to give the second equivalent of benzyl chloride and silyl ether.
