A Simple, Efficient, and General Method for the Conversion of Alcohols into Alkyl Iodides by a CeCl 3 ·7H 2 O/NaI System in Acetonitrile (original) (raw)
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Molecular Diversity, 2019
Aldehydes and ketones are parts of millions of compounds and are important classes of chemicals which serve as important precursors for the synthesis of library of compounds. For the synthesis of aldehydes and ketones, one impressive approach to date, because of its excellent selectivity, high yield and stability toward over-reduction and over-oxidation, is the oxidation of organic halides (viz. aliphatic and benzyl halides). The current review covers the conventional and eco-friendly transformational approaches, from 2000 to date, toward synthesis of aldehydes and ketones from organic halides, including mechanistic studies, comparison of different transformational strategies and discussion on scope and cons and pros of each transformational approach. The review would be beneficial to get knowledge about recent synthesis techniques, select finest synthetic approach, develop further new transformational methodologies and improve current transformational approaches.
ES Critical Reviews: Transformations of halogenated aliphatic compounds
Environmental Science & Technology, 1987
Bansformations of halwenated aliphatic cornpun& oxidation. r e d d o n , substitulion, and akhydrohalogerdon reactions occur abwtidly or in m i d i a l and mammalian systems otic and biotic chemistry of halogenated aliphatic compounds. Knowledge of cxmcqld tiamavo& for understand-abiotic aansformatloos ' canprovidea tiolls. Mast abiotic transformations are slow, but t&ey urn stiU be significaa withinthetimescalescommonly associated with groundwater m o v m. In contrast, biotic transformations typid y proceed much faster, provided that there are sufficient substrate and nutrients and a microbial poprlation that canldiate SUChtransformations. Recent studies, which describe transformations of halogenated aliphatic canpounds in mi&i and lIwnmal i a n s y m , are akodiscussedinthis systemingeneral. ing bidogicalhl mediated t r a n s f~marticle. These studies reveal broad patterns of transformalion in biological All three systems (abiotic, mammalian, and microbial) have similarities in r r-TABLE 1 Production, proposed maximum contaminant levels, ratings of comnlon halogenated aliphatic compounda Compound Trihalomethanes Vinyl chloride 1 .l-Dichlorcethylene trans-I ,2-Dichloroethylene Trichloroethylene Tetrachloroethylene 1,l-Dichloroethane 1.2-Dichloroethane 1 ,1, 1-Trichloroelhane 1 ,BDibromoelhane .Reference 4. 'Maximum mntaminenl level. Reference 5. <Carcinogenicity: 1 = chemical is carcinr^^^'^' chemical cannot be classified. bReference 6. reaction mechanism and transforma-I ences. For each, the transformation of halogenated aliphatic compounds can that q* ~~~~yydrohalogenation-elimina-lonizatbn potential-thi dil-fer (oxidations and reductions) and tion of HX to form an alkene, ence between the energy of ultra Dlhalo-elimination-reductive let radiation used to bombard a mc+ those that do not (substitutions and deh y~' % e M t i m)~ External elimination of two halide substi-ecule and the energy of the ejected transfer i s as the transfer Of tuents to form an alkene. electron. e1-m to and from some agent other Electwhi16e reacting specie Yonooxygenase-an enzyme than the that accepts an electron pair. that catalyzes reactions in which one Eiiiinatlon-a reaction in which atom of O2 appears in the product Processesin this article and terms that frequently appear = detwo groups, such as hydrogen and and the other in H a. f i in the side E-1-Of trans-Nudeophila-a reacting specie chlorine, are lost from adjacent car-f0nnatiOm are listed in Figure 1. COmbon atoms so that a double bond is that brings an electron pair. mon abbreviations for the various Sohrolysls-a reaction in which for&. halogenated aliphatic Compounds are Epoxldation-a reaction in which the solvent serves as the nulisted in Table 2. an epoxide is generated. cleophiie. Substitutiin-a reaction in wh ~ ~ Hydro@%noly&i-a reduction in substitution which a carbon-halogen bond is one substituent on a molecule is Halogenated aliphatic compounds ken and hydrogen replaces the placed by an0t'-undergo substitution and dehydmhalo-PERMISSUN m USE PICMAN WAS GIVEN BY A T A R I GAMES. tion products. They also have differbe divided into classes: re-Definitions of terms Coupling-a reaction in which halogensubstituent. Hydroxylation-addition alkyl or aryl groups connect tcdroxyl gmP. ' systems (Table 4) (22-29). Glutathione reacts with halogenafur-containing compounds. Under turic acids (28). Some chlorinated alkanes are transformed into alcohols in 724 Envimn. Sei. TBchnol., W. 21. No. 8. Igs7 strength may inrrease the L i l i o o d of creased stability of charged imermedicompounds more readily than is chloted aliphatic compounds to produce sulproper conditions, these compounds are further trrmsformed into mercap