2-phenylcyclopentanone oxime

diethyl ether

chlorine

pentane

alumina

drikold (solid CO₂)

acetone

ethanol

benzene

chloroform

 2-phenylcyclopentanone oxime (0.5 g) was dissolved in diethyl ether (15 ml), the flask, containing the solution, was cooled in ice  and a slow stream of chlorine was passed into the solution through a delivery tube until the blue colour, which first formed, changed to green. The excess chlorine and the ether was removed in the fume cupboard in a stream of air and the residue dissolved in pentane, the solution washed with water , separated, and the solution dried over sodium sulphate, then passed through a column of alumina and the blue eluate concentrated and then cooled, with drikold and acetone, to afford a blue solid which was filtered off, placed in an agate mortar , and on warming melted to a blue oil (0.2 g., 34%). After a few days in a refrigerator, the oil solidified to a colourless solid which was then ground to a colourless amorphous solid. It dissolves slowly in benzene, more readily in chloroform.

Very few dimeric gem-chloronitroso compounds have been reported.

Work in subdued light. When solutions of the monomer in ethanol or benzene are exposed to red light a hypsochromic shift of 5 nm and a reduction of ε_max was observed.     Absorption measurements were consistent with a fairly rapid photomutarotation followed by a much slower photolysis.

Solid began to turn blue at 78°, mp 84°

Found: C 63.23%, H 5.66%, Cl 16.69%, N 6.60%  (C₁₁H₁₂ClNO)₂ requires: C 63.01%, H 5.77%, Cl 16.91%, N 6.68%    ε _max 44 at  643 nm (in benzene)

Cryoscopic measurements gave a molecular weight of 205. Calc. for C₁₁H₁₂ClNO: 209.7 and Beer’s Law holds over the range studied (up to 1%)

K. A. Ogloblin, T. N. Grigorova, and A. A. Potekhin, Zhurnal Organicheskoi Khimii, 5, 1360-1363 (1969) (English translation 1329-1332)

Mohamed-Cherif Boucenna, John S. Davidson, Anthony McKee, Andrew L. Porte, and David C. Apperley, J. Chem. Soc., Perkin Transactions. 2, 1381-1387 (1995) doi: 10.1039/P29950001381

A. J. N. Hope and Stotherd Mitchell, J. Chem. Soc., 1953, 3483-3486; 1954, 4215-4218