10535-35-0Relevant academic research and scientific papers
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.
ACID-BASE REACTIONS OF 1,3,4-THIADIAZOLINES AND THIOCARBONYL YLIDES; 1,3,4-THIADIAZOLINE-2-SPIRO-2'-ADAMANTANE
Mloston, Grzegorz,Huisgen, Rolf
, p. 1053 - 1056 (2007/10/02)
The surprising formation of C22H32N2S2 from the title compound 1 at 45 oC involves the interaction of the basic adamantanethione S-methylide (2) with its acidic precursor 1, in the course of which the anion 6 undergoes electrocyclic ring opening; the acid and base functions offer the clue to a prolific chemistry of the thiadiazoline 1 and the thiocarbonyl ylide 2.
