SYNTHESIS OF ORGANIC DEUTERIUM COMPOUNDS: PART VI. FORMALDEHYDE-d2 AND FORMALDEHYDE-d

Abstract

Formaldehyde-d2 was prepared in 62.5% over-all yield from 1,2-dibromoethane-d4 via the corresponding glycol diacetate and glycol. Formaldehyde-d was prepared by the same method from sym-1,2-dibromoethane-d2. From the high isotopic purity of the deuterated formaldehydes obtained, it has been definitely established that it is a pair of hydrogen atoms from the hydroxylic groups of the glycols that generates acetic acid during dialdehyde fission with lead tetraacetate. The densities and refractive indices of the deuterated ethylene glycol diacetates and ethylene glycols used as intermediates in the synthesis of the deuterated formaldehydes have been determined.