1‐Chloro‐1‐nitrosocyclohexane

[695-64-7] C6H10ClNO (MW 147.5) InChI = 1S/C6H10ClNO/c7-6(8-9)4-2-1-3-5-6/h1-5H2 InChIKey = NJGFNBVUIGJGOK-UHFFFAOYSA-N (electrophilic [NH2+] for alkenes and can function as a dienophile for [4 + 2] reactions) Alternate Name: cyclohexane, 1-chloro-1-nitroso-. Physical Data: bp 52 °C/12 mmHg. Solubility: sol in wide range of organic solvents. Form Supplied in: solid; widely available. Preparative Methods: the most commonly used method is the reaction of cyclohexanone oxime with a chlorinating agent such as t-Butyl Hypochlorite in trichlorofluoromethane (eq 1).1 (1) Methods for preparation or in situ generation are generally based on treatment of cyclohexanone oxime with an electrophilic chlorinating source such as tert-butyl hypocholorite,1, 7 elemental chlorine,8, 9 aqueous hypochlorous acid,10 or N-halo compounds.11, 12 Recently, in 2011, Motherwell introduced a new protocol that avoids the necessity of using an electrophilic halogen atom via reaction of the nitronate anion derived from nitrocyclohexane with oxalyl chloride (eq 2).13 (2) Handling, Storage, and Precautions: may explode during vacuum distillation. When heated to decomposition it emits toxic fumes of HCl and NOx.