An efficient synthesis of both enantiomers of trans-1, 2-cyclopentanediol and their conversion to two novel bidentate phosphite and fluorophosphinite ligands

AF Cunningham Jr, EP Kuendig

Index: Cunningham, Allan F.; Kuendig, E. Peter Journal of Organic Chemistry, 1988 , vol. 53, # 8 p. 1823 - 1825

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Citation Number: 60

Abstract

Attempted cycloalkylation under phase-transfer conditions (50% NaOH/tol~ ene/NBu, I~~) resulted in complete recovery of the starting materials. Heating the dibromide 7 with 2 equiv of the sodium salt of bis (pheny1-sulfony1) methane in DMF at 75 OCI5 resulted in the loss of 7 without yielding the desired cyclic product 8. However, when a 1: l mixture of 7 and bis (pheny1-sulfony1) methane was stirred in a suspension of KzC03 in DMF at 75 OC for 20 ...