Studies in Stereochemistry. XX. dl-Phenylserinols : A New Synthesis and its Stereochemical Findings. (7). An Isomerization of dlthreo-2-Phenyl-4-α-hydroxybenzyl-2-oxazoline to dl-threo-4-Hydroxymethyl-2, 5-diphenyl-2-oxazoline in Basic Media : The Correction of the Previously Proposed Structure for the Isomerization Product.

抄録

In the preceding paper of this series, it was tentatively assumed, while leaving some doubt, that dl-threo-2-phenyl-4-α-hydroxybenzyl-2-oxazoline isomerized into dl-2-benzamido-3-phenyl-2-propen-1-ol or dl-2-benzimido-3-phenylpropanol in basic media. In this paper, the structure of the isomerization product was corrected to dl-threo-2, 5-diphenyl-4-hydroxymethyl-2-oxazoline by reexamination of chemical properties and final synthesis. The analogous isomerization observed in the optically active p-nitro analogs is a further support for the correction and a possible mechanism of the isomerization without Walden inversion was proposed. dl-threo-2, 5-Diphenyl-4-benzoyloxymethyl-2-oxazoline was found to add benzoyl chloride causing ring opening with Walden inversion to give dl-erythro-2-dibenzoylamino-3-chloro-3-phenylpropyl benzoate.