Acid–base reactions of adamantanethione S -methylide and its spiro-1,3,4-thiadiazoline precursor
作者： Grzegorz Mloston , Rolf Huisgen
DOI: 10.1016/S0040-4020(00)00988-1
关键词: Ring (chemistry) 、 Stereochemistry 、 Acid–base reaction 、 Ion 、 Acid catalysis 、 Base (chemistry) 、 Chemistry 、 Medicinal chemistry 、 Adamantane derivatives
摘要: Abstract 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 CH2-protonation and ion recombination. Even acts vs and—after electrocyclic ring opening anion (13 →15)—affords dithioacetal C22H32N2S2 (14). Δ3-thiadiazoline converted base or acid catalysis to Δ2-tautomer 21. Amidrazones (25, 26) are formed from sec-amines. mechanisms discussed structures elucidated.
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