Synthesis of [C5 (CH3) 4H] CH2CH2CH2P (C6H5) 2: a novel heterodifunctional ligand possessing both a tetramethylcyclopentadiene and a remote …

…, EA Mintz, SJ Sussangkarn

Index: Bensley, Dennis M.; Mintz, Eric A.; Sussangkarn, Susan J. Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4417 - 4419

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Citation Number: 34

Abstract

Treatment of 4 and 5 with p-toluenesulfonyl chloride in pyridine, followed by the usual workup, produces 3-(tetramethylcyclopentadieny1)-1-(P-tolylsulfony1) propane (6)(three tautomers) in 74% yield, with no detectable amount of the exocyclic double bond tautomer as determined by'H and 13C NMR. Apparently, during the acidic workup, the exocyclic double bond isomerizes into the ring producing only 6.