Ring–chain tautomerism ‘frozen-out’ by crystal packing forces: 13C n.m.r. spectroscopy and the remarkable crystal structure of the bromohydrin of 7,7-dichlorobicyclo[3.2.0]heptan-6-one
Abstract
X-Ray structure analysis of the title compound shows it to exist as a remarkable 1 : 1 mixture (in a single crystal) of ring–chain tautomers and which are detectable by n.m.r. spectroscopy in acidified CHCl3 as an equilibrium mixture varying between 1 : 1 to 1 :2·8 over the range 238–304 K.