𝔖 Bobbio Scriptorium
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Proton Exchange between Arenium Ions and Arenes in the Gas Phase

✍ Scribed by Dr. Dietmar Kuck; Dr. Steen Ingemann; Leo J. de Koning; Prof. Dr. Hans-Friedrich Grützmacher; Prof. Dr. Nico M. M. Nibbering

Publisher
John Wiley and Sons
Year
1985
Tongue
English
Weight
320 KB
Volume
24
Category
Article
ISSN
0044-8249

No coin nor oath required. For personal study only.

✦ Synopsis

Experimental procedure: 2 : 30% H 2 0 2 (11.3 g, I00 mmol) was added with stirring to ethyl pyruvate (17.3 g, 150 mmol) at -10 to 0°C [3]. This solution was then added with stirring and cooling (-5 to 0°C) to a mixture of I (10 mmol), conc. H S O J (3 g), H 2 0 (8g), F e S 0 4 . 7 H 2 0 (28 g, 100mmol), and CH?CIZ (150mL). After 15 min of further stirring, the resulting mixture was poured into ice water, the phases were separated, and the aqueous phase was exhaustively extracted with CH2C12. After drying over anhydrous Na2S0,, the solvent and excess ethyl pyruvate were removed in vacuo. The spontaneously crystallizing, colorless needles were recrystallized from diethyl ether: Yield: 1.4g (81Yo) 2 ; mp=X%93"; correct C,H,N analyses. IR (KBr): 1715 (v(.="), 2250 c m -' (vCsN): MS: m/z 176 (2%, M + ) , 104 (100%): 'H-NMR (CDCI,, 90 MHz): 6=9.00 (d, 1 H, J = 5 Hz, H-6), 8.39 (d, 1 H, J = 2 Hz, H-3), 7.75 (dd, I H, J = 5 Hz, 2 Hz, H-S), 4.53 (4, 2 H , J = 7 Hz, CHI), 1.48 (t. 3 H , J = 7 Hz, CHI).

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