The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Interaction of hydroxy compounds and phosphorus and thionyl halides in the absence and in the presence of tertiary bases. VI》. Authors are Berlak, Marianne C.; Gerrard, Wm..The article about the compound:1-Iodo-2-methylbutanecas:616-14-8,SMILESS:CCC(CI)C).Related Products of 616-14-8. Through the article, more information about this compound (cas:616-14-8) is conveyed.
cf. C.A. 41, 93d. The following yields (in %) of alkyl iodide were obtained from the resp. alc. and 0.33 mol. PI3 in CS2 at 15-20° in 24 h. (other exptl. conditions indicated): PrOH 40; iso-PrOH 20 (72 h. 21; 1 mol. 18); BuOH 43 (72 h. 61, 2.5 h. at b.p. 48; 1 mol. for 24 or 72 h. 56); sec-BuOH 60 (72 h. 58; 1 mol. 61); tert-BuOH 20 (also 72 h.; 1 mol. 17); sec-BuCH2OH 48 (68 h. 44, 1 mol. 45); Pr2CHOH 74 (1 mol. 80); C8H17OH 42 (1 mol. 56); C6H13CH(Me)OH (I) 36 (0.66 mol. for 24 or 72 h. 66, 1 mol. 75). (+)-I (6.5 g.) and 3.95 g. C5H5N in 50 cc. CS2 at -10°, treated with 6.9 g. PI3, give 9.3 g. C5H5N.HI; further addition of 13.8 g. PI3 gives 7.78 g. C6H13CHIMe, αD18 -56.8% BuOH and C8H17OH show a similar behavior. (-)-Dimethylhexylcarbinyl H phosphite (4.6 g., αD22 -12.6°) at -10°, treated (1 h.) with HI and kept 18 h. at 15° gives 5.93 g. (+)-C6H13CHIMe, αD20 45.8°. (BuO)2PHO (6.5 g.), treated 50 min. at -10° with HI and kept 30 min. at -10°, gives 2.65 g. BuI; if the reaction is carried out without cooling (temperature rise from 19 to 23°), there results 5.3 g. BuI. (RO)2HPO react much more readily with HI than with HCl or HBr. The mechanism of the reaction is discussed.
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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem