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. Author manuscript; available in PMC: 2013 Jul 6.
Published in final edited form as: Org Lett. 2012 Jun 21;14(13):3264–3267. doi: 10.1021/ol301154f

Table 3.

Reactions of 5a with Various Benzylic Alcohols

graphic file with name nihms388263u4.jpg
entry Nu R1 R2 E:Za,b yield (%)c
1 4m Me H 1:3 8a, 60
2 4n Cyclopropyl H 1:3 8b, 72
3 4o Ph H 1:5 8c, 60
4 4p CF3 H 1:4 8d, 67
5 4q Me Me — 8e, 0
a

Ratio determined from the 1H NMR spectrum of the crude product.

b

The E isomers were difficult to purify and characterize, due to the presence of other byproducts.

c

Isolated yield of the major (Z) phthalan.