Ether, benzyl ethyl analysis

As could have been seen from an analysis of the product during the course of the reaction, only the hydrodechlorination of 3c took place. No other possible dehalogenated products, e.g., benzyl alcohol or benzyl ethyl ether, were detected. This might explain why, particularly in the case of catalyst Pd 1C, the chlorosubstituted benzyl ether (4b) was the only product formed in high yield. Because of the kind and strength of acidity,... 

A solution of ethyl diazoacetate (2.0 mmol) in benzene or cyclohexane is added by syringe pump over 24- 30 h to a slirred mixture of 0.1 mmol of Rh,(OAc)4 and 10-20 mmol of the allylaminc 14 at 60 "C. Following complete addition, the reaction mixture is diluted with Et,0, the resulting solution is extracted with sat. aq NaHCOj. and the products are isolated by standard procedures. Isolated yields are determined by GC using an internal standard (benzyl ether). Diastereomeric separations and analyses arc obtained by GC analysis (2-m Carbowax 20 M column). 

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