The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Primary active amyl halides》. Authors are Whitmore, Frank C.; Olewine, J. Harris.The article about the compound:1-Iodo-2-methylbutanecas:616-14-8,SMILESS:CCC(CI)C).SDS of cas: 616-14-8. Through the article, more information about this compound (cas:616-14-8) is conveyed.
Primary active AmOH (I) with SOCl2 in C5H5N give 77% of the AmCl, b140 50.5-1°, nD20 1.4125, n420 0.8852, [α]D28.5 1.66°. I and PBr3 at 5-15° give 29% of the AmBr, b140 69.6°, nD20 1.4450, d420 1.2239, [α]D25 3.75°. I and BzCl give 80% of the benzoate, b20 140.2°, nD20 1.4948, d420 0.9913, [α]D28 6.09°; with MeMgI this yields 17.5% of the AmI, b20 47.1°, nD20 1.4969, d42 1.5227, [α]D28 4.84°. Data are given for the constants of I after regeneration from the chloride or bromide through the Grignard reagents; the total racemization in the steps I → AmCl or AmBr → Grignard reagent → I is not over 10%.
Different reactions of this compound(1-Iodo-2-methylbutane)SDS of cas: 616-14-8 require different conditions, so the reaction conditions are very important.
Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem