Bromocamphor-8-sulfonic Acid

Miyano,S. Hattori, T Uesugi, S. Tamai, Y. Sayo, N., Jpn. Kokai Tokkyo Koho (CAN 131 228639) 1999. 

David R. Williams David C. Kammler Indiana University, Bloomington, Indiana, USA 

Solubility the ammonium salt is sol in water, slightly sol in EtOH, but essentially insol in acetone and Et20. The free acid is sol in EtOAc, MeCN, and 5% aq. NaOH. 

Form Supplied in both enantiomers are commercially available as ammonium salts. 

Handling, Storage, and Precautions a 0.5 M solution of the free acid in dry MeCN is stable for at least 30 days at 5 °C in a closed vessel under N2.  

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R( e/ido,a/i/()-3-Bromocamphor-8-sulfonic acid ammonium salt see entry in Chapter 5. 

Phenyl-6-nitroBIPS was easily resolved (at the 3 -carbon atom, not the 2 -spiro position) by reaction in ethanol with either (+) or (-) 10-camphorsulfonic acid. The first fraction to crystallize in each case was the salt of the open form. Both salts had a mp of 237°C and their solutions, after standing to thermally equilibrate at the 2 -carbon atom, showed equal but opposite rotations, [oc]d25 = -201° for the salt from the (+) sulfonic acid and +201° for the salt from the (-) acid. After treatment of these salts with aqueous sodium acetate and benzene, the respective spiropyrans, having melting points of 201-202°C and specific rotations of -11° and +11° for thermally equilibrated solutions, were recovered from the benzene extract. Similar attempts to resolve several other 3 -phenylBIPS with the camphorsulfonic or 3-bromocamphor-8-sulfonic acids were only pardy successful.7... 

Chemical Resolution of Compounds Containing Basic Groups. 3-Bromocamphor-8-sulfonic acid has been widely used as a resolving agent for compounds containing basic groups. A number of primary (1), secondary (2), and tertiary (3) amines as well as oxazolines (4) have been resolved by the formation of diastereomeric salts derived from 3-bromo-8-camphorsulfonic acid. 

The optical resolution of racemicp-hydroxypheny Iglycine with 3-bromocamphor-8-sulfonic acid has also been achieved. This resolving agent has also been widely used in the preparation of optically pure chromium and cobalt complexes. ... 

Preparation of Chiral Reagents. 3-Bromocamphor-8-sulfonic acid has been used as a starting material for the synthesis of chiral reagents. Although the oxidation of sulfides to sulfoxides can be accompUshed with the oxaziridine (5) or (6),... 

Related Reagents. 3-Bromocamphor-8-sulfonic Acid (—)-(lS,4iJ)-Camphanic Acid 2,4,6-Collidinium p-Tolu-... 

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