66673-27-6Relevant articles and documents
Acid-base reactions of adamantanethione S-methylide and its spiro-1,3,4-thiadiazoline precursor
Mloston, Grzegorz,Huisgen, Rolf
, p. 145 - 151 (2007/10/03)
The spiro-1,3,4-thiadiazoline 1 loses N2 at 45°C, and, as recently reported, the short-lived adamantanethione S-methylide (2) is an active 1,3-dipole. Interception of 2 by acids HX consists of CH2-protonation and ion recombination. Even 1 acts as HX vs 2 and - after electrocyclic ring opening of the anion (13 →15) - affords the dithioacetal C22H32N2S2 (14). The Δ3-thiadiazoline 1 is converted by base or acid catalysis to the Δ2-tautomer 21. Amidrazones (25, 26) are formed from 1 and sec-amines. The mechanisms are discussed and the structures elucidated.
Unexpected Transformations of Camphor (Thio)Semicarbazones under Acetylating Conditions
Somogyi, Laszlo
, p. 1267 - 1272 (2007/10/02)
The formation of camphor mono- and diacetylhydrazones (1, 4, 6) and a stereoselective synthesis of the spirothiadiazoline (1R)-(+)-2 is described.The degradation of (thio)semicarbazones 3 (X = O, S) and diacetylhydrazone 4 to the acetylhydrazone 6 has bee