抄録
It has previously been reported that the application of fuming sulfuric acid to α, π-dihalo-d-camphor resulted in isomerization to form 6-trans-π-dihalo-ι-camphor. Two kinds of dihalocamphorsulfonic acids, unknown to date, were separated from the sulfuric acidmother liquor obtained as a by-product by the foregoing isomerization on α, π-dichloro-and α-chloro-π-bromo-d-camphor, and these were confirmed to be α, ω-dichloro-d-camphor-trans-π-sulfonic acid (IV) and α-chloro-ω-bromo-d-camphor-trans-π-sulfonic acid (IV′). These two kinds of sulfonic acids easily undergo desulfurous acid reaction in aqueous acid solution to give α, ω-dichloro-trans-π-hydroxy-d-camphor (V) and α-chloro-ω-bromo-trans-π-hydroxy-d-camphor (V′), respectively. The dihalohydroxycamphors were derived to α, ω-dichloro-trans-π-bromo-d-camphor (IX), α-trans-π-dichloro-ω-bromo-d-camphor (IX′), ω-chloro-trans-π-hydroxy-d-camphor (VI), and its oxidation products, ω-chloro-trans-π-keto-d-camphor (VII), and ω-chloro-d-isoketopinic acid (VIII), which are all new compounds.
