oxymercuration n.
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1. 2. Oxymercuration. Total of 8 racemates possible. Only 2 are formed. 2. kinetically controlled; high energy TS’s ≠. kinetically controlled; low energy TS’s ≠. 1. 1. 2. Oxymercuration – II; Add a Methyl Group. regiochemistry ; anti addition; Markovnikov.

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oxymercuration

1

2

Oxymercuration

Total of 8 racemates possible. Only 2 are formed.

2

kinetically controlled; high energy TS’s≠

kinetically controlled; low energy TS’s≠

1

oxymercuration ii add a methyl group

1

2

Oxymercuration – II; Add a Methyl Group

regiochemistry; anti addition; Markovnikov

regiochemistry; anti addition; anti - Markovnikov

wrong regiochemistry

boatlike TS≠ eliminated on previous slide

Only product!!!

oxymercuration iii

Oxymercuration - III

If BD4- had been used as the reductant, a mixture of deuterio compounds would form.

oxymercuration iv

diastereomers

Oxymercuration - IV

anti addition; Markovnikov

diastereomers

radical intermediate

anti addition; Markovnikov

slide5

Alkyl Mercurials – Radical Oxygenation

endo

Endo and exomercurials give the same radical.

Product distributions the same.

exo

RHgBr + BH4- --------> RHgH

RHgH ---------> R . + .HgH

R . + O2 ---------> ROO .

ROO . + .HgH -------> ROOH + Hg0

ROOH + BH4- --------> ROH

= R

C. L. Hill and G. M. Whitesides,

J. Am. Chem. Soc., 96, 1974, 870.