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. Author manuscript; available in PMC: 2018 Jun 5.
Published in final edited form as: J Am Chem Soc. 2017 Sep 18;139(38):13562–13569. doi: 10.1021/jacs.7b07792

Table 1.

Timepoint analysis for the solvolytic cyclization of enantioenriched dihalides.

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(A) aPrepared as a >20:1 mixture of constitutional bromochloride isomers.

b

1.5 equiv. K2CO3, 0.05 M in HFIP.

c

Based on 1H NMR analysis using 1,4-dinitrobenzene as an internal standard.

d

According to chiral HPLC analysis.

e

Ratio of constitutional isomers according to 1H NMR analysis.

f

HPLC integration was complicated by the presence of the corresponding constitutional isomer.

(B) Proposed mechanism for equilibration of bromochloride constitutional isomers and racemization of dibromides.