1964
DOI: 10.1021/jo01026a054
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Cyclic Imidocarbonate Hydrochlorides from the Reaction of Cyanogen Chloride with Dithiols and Diols

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Cited by 39 publications
(11 citation statements)
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“…The acid-catalysed reaction of alcohols with 1 may be rationalized in terms of an initial addition of HC1 to 1 with the formation of the very reactive electrophilic intermediate -10, which in the presence of the alcohol subsequently forms the alkyl imidocarbonate hydrochloride 2 via 11 releasing HC1. Similarly to the cyclic imidocarbonate hydrochlorides (11) , -12 decomposes under the reaction conditions into the corresponding carbamate 3 and the alkyl chloride 4. The steps (1) to ( 3 ) correspond to the mechanism already proposed by Addor (11) for the reaction of dithiols and diols with 1.…”
Section: Discussionmentioning
confidence: 99%
“…The acid-catalysed reaction of alcohols with 1 may be rationalized in terms of an initial addition of HC1 to 1 with the formation of the very reactive electrophilic intermediate -10, which in the presence of the alcohol subsequently forms the alkyl imidocarbonate hydrochloride 2 via 11 releasing HC1. Similarly to the cyclic imidocarbonate hydrochlorides (11) , -12 decomposes under the reaction conditions into the corresponding carbamate 3 and the alkyl chloride 4. The steps (1) to ( 3 ) correspond to the mechanism already proposed by Addor (11) for the reaction of dithiols and diols with 1.…”
Section: Discussionmentioning
confidence: 99%
“…in Cyclohexan (loge): 239 (4,22); 254 (4,25); 304 (3,82); 337 nm (3,GO (23,3%), F. 32 "C (Petrolather, A , , , in Cyclohexan (loge): 220 (4,13); 265 (4,22); 332 nm (3,41). C,H,NS,(213,l) Ber.…”
Section: mentioning
confidence: 99%
“…61%, F. 134 "C (Zers.). 50 (4,06); 289 (5,32); 349 nm (2,65 in Methanol (log&): 229 (4,OG); 269 (3,04); 309 (3,.53); 362 nm (3," 3,.5 g (14,G?/,), undestillierbares 81. A , , , in Cyclohesan (log&): 230 (4,27); 269 (4,30); 307 S (3,73); 351 nm (3,OO).…”
Section: -Azido-4s-tetramethylen-13-dithiol 2 Bmentioning
confidence: 99%
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“…The structure of this material was shown by infrared and nuclear magnetic resonance spectroscopy to be 2-(dichlorophosphinylimino)-5-methyl-l,3-dithiolane (Addor, 1964). Equimolar amounts of 2-imino-5-methyl-l,3-dithiolane hydrochloride and phosphorus oxychloride were refluxed approximately 3 h in toluene until the theoretical amount of hydrogen chloride was eliminated and most of the solids disappeared.…”
Section: Synthesis Of [13c]mephosfolan ( I ) Imido Carbonmentioning
confidence: 99%