Silica gel triggered transformations of 3-methylenecyclopropylmethyl sulfonates to 3-methylenecyclobutyl analogues: Experimental and computational studies

Chemistry - A European Journal

Volumn 13, Issue 3, 2007, Pages 862-869

  Shao, Li Xiong ^a   Li, Yu Xue ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Density functional calculations; Methylenecyclopropylcarbinols; Rearrangement; Silica gel; Synthetic methods

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; PROBABILITY DENSITY FUNCTION; SILICA GEL; SULFONATION;

METHYLENECYCLOPROPYLCARBINOLS; REARRANGEMENT; SYNTHETIC METHODS;

AROMATIC COMPOUNDS;

EID: 33846419522     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600722     Document Type: Article

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48. Substrate 1m was synthesized from methylation of the corresponding aldehyde with methylmagnesium bromide and the diastereoisomers can be separated by silica gel column chromatography. We only use one of the diastereoisomers for the rearrangement reaction. At present stage, we did not determine the relative configuration of 1m shown in Scheme 4. It also should be noted that only one isomer was obtained for product 4q-1 or 4q-2, respectively.