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. Author manuscript; available in PMC: 2011 Oct 20.
Published in final edited form as: Tetrahedron Lett. 2010 Oct 20;51(42):5615–5617. doi: 10.1016/j.tetlet.2010.08.068

Table 2.

Fragmentation of hydroperoxyacetals with t-BuOCl

graphic file with name nihms231871u2.jpg
Entry Substrate t-BuOCl (eq) t(min) Product Yielda
1 1a 1.2 10 2a 77%
2b 1a 1.2 10 2a 77%
3c 1a 1.2 10 2a 79%
4d 1a 1.2 10 2a 84%
5 1a 0.25 15 2a 78%
6 1b 1.2 10 2b 85%
7 1d 1.2 10 2d 84%
8 1e 0.25 15 2e 85%
9 1h 1.2 10 2h 84%
a

Isolated yields on 0.5 mmol scale.

b

Protected from light (Al foil over flask).

c

CH2Cl2 as solvent.

d

Added HOAc (≥ 2 eq)