2013
DOI: 10.3762/bjoc.9.195
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The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives

Abstract: SummaryWith the goal of eventually synthesizing [5]radialene (3), the still missing member of the parent radialene hydrocarbons, we have prepared the pentaacetates 21 and 31, the pentabromide 29 and the hexabromide 32. In principle these should be convertible by elimination reactions to the desired target molecule.

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Cited by 11 publications
(11 citation statements)
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References 12 publications
(24 reference statements)
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“…1,1,2,3,4,5,6,7‐Octa(methoxycarbonyl)cyclohepta‐2,4‐diene (3a) and 1,1,2,3,4,5,6,7‐Octa(methoxycarbonyl)cyclohepta‐3,5‐diene (3b): A mixture of dimethyl dibromosuccinate 5 (3.45 g, 11.4 mmol), dimethyl malonate (0.50 g, 3.8 mmol), pyridine (1.8 g, 22.7 mmol), and DMF (1.8 mL) stirred for 3 d. The mixture was poured into water (10 mL), decanted and the precipitate was stirred with diethyl ether (10 mL), filtered and washed with water and ether to give the desired mixture of cycloheptadienes 3a , 3b (1.08 g, 52 %). The physical data correspond to those previously reported …”
Section: Methodssupporting
confidence: 90%
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“…1,1,2,3,4,5,6,7‐Octa(methoxycarbonyl)cyclohepta‐2,4‐diene (3a) and 1,1,2,3,4,5,6,7‐Octa(methoxycarbonyl)cyclohepta‐3,5‐diene (3b): A mixture of dimethyl dibromosuccinate 5 (3.45 g, 11.4 mmol), dimethyl malonate (0.50 g, 3.8 mmol), pyridine (1.8 g, 22.7 mmol), and DMF (1.8 mL) stirred for 3 d. The mixture was poured into water (10 mL), decanted and the precipitate was stirred with diethyl ether (10 mL), filtered and washed with water and ether to give the desired mixture of cycloheptadienes 3a , 3b (1.08 g, 52 %). The physical data correspond to those previously reported …”
Section: Methodssupporting
confidence: 90%
“…We have shown herein that DMAD ( 2 ), which is conventionally used for the generation of vinylpyridinium 7 , could be substituted with dimethyl dibromosuccinate 5 in the reaction with dimethyl malonate to give the mixture of tautomeric cycloheptadienes 3a , b in a yield of 52 %. It is noteworthy that the ratio of tautomers 3a , b depends to a large extent on the work‐up as it was previously noted for the conventional syntheses . DMAD is polymerizable, lachrymatory and vesicant while dimethyl dibromosuccinate is a crystalline, non‐volatile substance, which is easily available from cheap succinic acid.…”
Section: Resultsmentioning
confidence: 81%
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