The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Acid iodides. II. The cleavage of aliphatic ethers by acid iodides》. Authors are Gustus, Edwin L.; Stevens, Philip G..The article about the compound:2-Chloroethyl acetatecas:542-58-5,SMILESS:CC(OCCCl)=O).Application of 542-58-5. Through the article, more information about this compound (cas:542-58-5) is conveyed.
When an aliphatic ether is treated with AcI, the reaction mixture becomes warm after a short induction period of often less than a min. This heat is soon dissipated. If the mixture is allowed to stand at room temperature for 2-5 days, it is found that the ether has been cleaved with the formation of an alkyl iodide and an alkyl acetate. This reaction proceeds much faster with di-sec. than with di-primary ethers. The mol. weight of primary ethers appears to influence slightly the ease with which they are cleaved. In the cleavage of unsym. aliphatic ethers, it is found that, with di-primary ethers, the greater proportion of I is attached to the smaller alkyl group. With mixed primary-sec. ethers about 0.5 of the I went to the smaller (in this case the primary) radical; in addition, rearrangement products appeared. The structure of the acid iodide in ether cleavage is almost as important as the structure of the ether itself. The introduction of Cl into the iodide has a marked effect. While thioethers are cleaved by acid iodides, the rate of cleavage is much slower than that of O ethers. Pr2O (12.25 g.) and 17 g. AcI, after 89 hrs., give 45.8% PrI, isolated as PrMe3NI and AcOPr. Details of yields are given for Me2O, Bu2O, iso-Am2O, iso-Pr2O and AcI. Et2S and AcI after 1296 hrs. still contained much unreacted AcI; the reaction products were EtI and EtSH. AcI and (CH2)2O in 20 hrs. give 73.8% of β-ICH2CH2OAc, b43 95-6°, nD20 1.5072; AcCl, after 44 days at 25°, gives about 95% of β-ClCH2CH2OAc; if a drop of concentrated HCl is added to the AcCl the reaction is completed in about 2.5 days, the yield of β-ClCH2CH2OAc being 78%; a small amount of I also catalyzes the reaction, 31% acetate being formed in 3.5 days at 25°; when equivalent amounts of AcI, (CH2)2O and I were used, the tube exploded on removal from the bath at -80°. AcCl, iso-Am2O and I remain unchanged after 44 days at 25°. Et2O and ClCH2COI, 5 days at 25°, give 91% EtI and 92% ClCH2CO2Et. Cl2CHCOI and AcI, after 6 days, give 91% of EtI and Cl2CHCO2Et. Cl3CCOI did not react with (iso-Pr)2O. MeOBu and ClCH2COI after 2 weeks give 73.2% MeI, 13.3% BuI and also ClCH2CO2Bu. Me(iso-Pr)CHOH, transformed into the K salt in p-cymene and treated with Me2SO4, gives methylisopropylcarbinol Me ether, b737 81.2-1.5°, d420 0.7586, nD20 1.3850; with ClCH2COI there results MeI (33.5%) and Me2C:CHMe. Methylisopropylcarbinol chloroacetate, b738 180-1°, d420 1.0418, nD20 1.4298. No reaction appears to take place between ClCH2COI and (ClCH2)2O after heating 6 days at 100°, or between Cl3CCOI and Et2O after 112 hrs. at room temperature or 3 hrs. at 100°, or with AcCl and Et2S after 1 week at 100°.
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