Reactions of. pi.-allylnickel bromide complexes with conjugated

The Synthesis of Coenzyme Q1 and. Plastoquinone-1. Sir : We report here a new and unusual reaction, the alkylation of quinones by a-allylnickel bromid...
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7155 Table I

-,

Reactant

Reagenta

Products (% y i e W 7 Solventb Linalool (7) Geraniol Nerol Limonene

1. Geranyl diselenide (5)

3Hzd2

THF-HzO

78

2. Geranyl diselenide (5)

3H202

THF-H2I80

75 (1000/0 Hz"O incorporation)

3. Geranyl diselenide (5) 4. Geranyl diselenide (5)

3H202 3HzOz

THF-CH30H Et20

75 (no methyl ethers) 41 18

10HzO2

THF-HtO

80

3H202

THF-H 2 0

70

3H202

THF-HzO

36

22

E?

4

13