Abstract
Chiral racemic 1,8-bis( tert-butylphenylphosphino)naphthalene oxide ( 2a) was resolved into enantiomers by fractional crystallization of its diastereomeric adducts 3a with (+)-(2 S,3 S)-di- O-benzoyl tartaric acid (DBTA), followed by neutralization. Racemic 1,8-bis( tert-butylphenylphosphino)naphthalene ( 1a) was oxidized with sulfur to two isomers of 1,8-bis( tert-butylphenyl-phosphino)naphthalene monosulfide, rac- 4a and rac- 4a′, or 1,8-bis( tert-butylphenylphosphino)naphthalene disulfide, rac- 5a. The compounds were characterized by NMR spectroscopy ( 1H, 31P, 13C). Crystal structures were determined by the X-ray method for (−)- 3a, rac- 4a, rac- 4a′ and rac- 5a; this allowed the determination of the absolute configuration ( S, S) for the more soluble adduct (−)- 3a. It was found that rac- 1a undergoes partial epimerization in boiling xylene to give the meso form.
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