George F. Wright
Apr 1, 1952
Citations
0
Influential Citations
12
Citations
Journal
Canadian Journal of Chemistry
Abstract
The reduction of 2-methoxyalkylmercuric halides by hydrazine hydrate is thought to proceed through mercuri-bis-2-methoxyalkane, which decomposes to give 2-methoxyalkarie radicals. These radicals may lose or gain a hydrogen atom to form 2-methoxyalkene or alkane. The reaction seems to be definitive for structure proof. The bis-mercurial from the (α) 2-methoxycyclohexylmercuric chloride which is formed directly from cyclohexene is less stable than the diastereomeric (β) bis-mercurial, which can be purified by distillation. Conversion of this (β) bis-mercurial to pure β-2-methoxycyclohexylmercuric chloride shows that this reaction occurs by direct replacement. The hydrazine reduction may be used to convert β-1-chloromercuri-2-methoxy-1,2-diphenylethane (from trans-stilbene) to the α-diastereomer. Since the β-isomer in this case is more readily hydrolyzable than the α isomer, and each isomer may be converted cleanly back to its parent alkene, the series of reactions provides a method of converting trans- into...