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. Author manuscript; available in PMC: 2014 Sep 3.
Published in final edited form as: J Org Chem. 2013 Mar 29;78(8):3989–3996. doi: 10.1021/jo400341n

Table 4. Chlorination of α-Branched Primary Alcohols.

graphic file with name nihms-623700-t0034.jpg

entry starting materiala product yieldb
1 graphic file with name nihms-623700-t0035.jpg graphic file with name nihms-623700-t0036.jpg 81%
2 graphic file with name nihms-623700-t0037.jpg graphic file with name nihms-623700-t0038.jpg 86%
3 graphic file with name nihms-623700-t0039.jpg graphic file with name nihms-623700-t0040.jpg 65%
a

Alcohol 10b is racemic.

b

Yield based on product isolated by flash chromatography.