820222-50-2Relevant academic research and scientific papers
Synthesis and rearrangement of [1,1′-bicyclobutyl]-1-ols and spiro[3.4]octan-5-ols: A general access to bicyclo[3.3.0]octenes (hexahydropentalenes)
Mandelt, Klaus,Meyer-Wilmes, Imelda,Fitjer, Lutz
, p. 11587 - 11595 (2007/10/03)
Several new Grignard reagents based on substituted cyclobutanes have been generated and added to cyclobutanones to yield mono- to trimethylated [1,1′-bicyclobutyl]-1-ols. Mono- to trimethylated spiro[3.4]octan-5-ols have been prepared from the parent ketone via alkylation and/or addition reactions. Upon treatment with acid, all [1,1′-bicyclobutyl]-1-ols and spiro[3.4]octan-5-ols rearrange to yield a single bicyclo[3.3.0]octene. Mono- to trimethylated [1,1′-bicyclobutyl]-1-ols and spiro[3.4]octan-5-ols have been synthesized and rearranged to yield a single bicyclo[3.3.0]octene in each case. Examples are 42, 43, 44 and 45.
