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. Author manuscript; available in PMC: 2014 Apr 5.
Published in final edited form as: J Org Chem. 2013 Mar 18;78(7):3452–3456. doi: 10.1021/jo4001564

Table 1.

Alkylation of dihydroperoxide 1a

graphic file with name nihms455042u2.jpg
entry electrophile methoda product (yield)
1 n-C10H21I A 2a (93%)
2 n-C10H21I C 2a (19%)b,c
3 n-C10H21I D 2a (7%) b,c
4 n-C10H21Br A or F -
5 n-C10H21I E -
7 n-C6 H13I A 2b (79%)
8 BnBr A 2c (56%)
9 graphic file with name nihms455042t1.jpg A 2d (79%)
10 graphic file with name nihms455042t2.jpg B 2d (80%)
11 Ph(CH2)4–OTf B 2e (68%)
12 2-iodooctane A -
13 2-iodooctane C 2f (trace)c
14 graphic file with name nihms455042t3.jpg B 2f (53%)
15 graphic file with name nihms455042t4.jpg B 2g (42%)
16 t-BuBr A monoalkylation (35%)
17 t-BuBr G NR
18 t-BuBr H -c
a

A: Ag2O, RBr or RI, EtOAc; B: KOtBu, ROTf, THF; C: CsOH•H2O (2 equiv), RI (2 eq) DMF; D: CsCO3 (2 equiv), RI (2 equiv), DMF; E: KOtBu (2.1 equiv), RI (2 equiv), THF; F: 50% KOH (4 equiv), RBr (2 equiv), n-Bu4NBr (10%), cyclohexane, 50 °C; G: K2CO3, acetone; H: K2CO3,DMF, 70 °C.

b

NMR-based yield (internal standard).

c

Decomposition of 1a with formation of ketone.