Chemical Properties
clear colorless liquid
Uses
Azetidine is involved in a high yielding palladium-catalyzed cross-coupling reaction with aryl bromides. Further, it is used in Ullmann type coupling reaction with iodonitroflourenes. In addition to this, it reacts with bis-(3-amino-propyl)-amine to prepare N,N'-bis-(3-amino-propyl)-propanediyldiamine using palladium as a catalyst.
Definition
ChEBI: Azetidine is a saturated organic heteromonocyclic parent, a member of azetidines and an azacycloalkane.
General Description
Phototransformations of azetidine radical cations in freonic matrices under the action of light with λ = 436nm has been investigated. The IR spectrum of azetidine in solid argon matrices has been measured.
Synthesis
To a 1-liter conical flask was added 4.0 mol of azetidine hydrochloride and 280 g of water, and the mixture was stirred at 20 degrees Celsius until the solid was dissolved, then to a 2-liter four-necked round-bottomed flask was added 230
g of water to which was added with stirring 459.4 g ( 6.96 mol
) of potassium hydroxide, and at the end of the exothermic addition of KOH, the solution was heated to 95 degrees Celsius and maintained at 95 degrees Celsius, an aqueous solution of azetidine hydrochloride ( 11 ) was added to the hot KOH
/aqueous solution, controlling the rate of addition, and completing the addition within 3 hours. After completion of the reaction, the target product, heteroazetidine, is obtained by slowly distilling and purifying the target compound.
Purification Methods
Azetidine is a flammable, hygroscopic liquid smelling of ammonia, which absorbs CO2 from air and should be kept under Argon. Purify it by drying it over solid KOH and distilling it through a short Vigreux column (p 11) at atmospheric pressure (under Argon) and keeping the pot temperature below 210o. It is moisture sensitive. The hydrochloride M 93.6 has m > 300o and the hydroiodide has m 146.5o(from EtOH). The N-Me derivative has m 112o(from *C6H6/pet ether), and the Nphenylcarbamoyl derivative has m 189-190o(from EtOH). [Searles et al. J Am Chem Soc 7 8 4917 1956, Beilstein 20 H 2, 20 I 3, 20 II 3, 20 III/IV 53, 20/1 V 136.]
