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The reaction of 3-bromocyclobutane-1-methyl bromide with sodium : bicyclo[1. 1. 1]pentane

✍ Scribed by Kenneth B. Wiberg; Daniel S. Connor; Gary M. Lampman

Publisher
Elsevier Science
Year
1964
Tongue
French
Weight
142 KB
Volume
5
Category
Article
ISSN
0040-4039

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✦ Synopsis

In recent years, the syntheses of a number of bicyclic small ring compounds such as the bicyclo[l. 1. Olbutanes, lr3 bicyclo[2. 1. Olpentane,"' bicyclo[Z. 2. Olhexane, 5r 6 the bicyclo[2. 1. llhexanes,' the bicyclo[3. I.01hexanes,' the bicyclo[3. 1. llheptanes." 1o and the bicyclo[3. 2. O]heptanesl" have been reported. The one member of this group for which no representatives have been obtained is bicyclo[l. 1. l]pentane although it appears to have a crucial role in the interpretation of the effects of bond angle deformation on the properties of compounds. Encouraged by our success in effecting a ring closure of l-bromo-3-chlorobutane to bicyclobutane using sodium, ' we have attempted a similar reaction with 3-bromocyclobutane-l-methyl bromide. This compound was prepared from methyl 3-methylenecyclobutane-1-CarboxylateI' by the anti-Markownikoff addition of hydrogen bromide followed by hydrolysis and brominative decarboxylation. I2 Chemistry, Methods and Results,

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