Chemistry of propadiene. II. The addition of dichlorocarbene to propadiene

The addition of dichlorocarbene to propadiene has been investigated. The reaction between propadiene and dichlorocarbene obtained from chloroform and potassium t-butoxide leads to tarry products. When generated by thermal decomposition of sodium trichloroacetate, the dichlorocarbene reacts with propadiene, yielding 1,1-dichloro-2-methylenecyclopropane (II). The structure of this compound was established by means of infrared and NMR spectroscopy and confirmed by chemical means.