Abstract
Abstract Arenesulfonic acids, their sodium salts, and alkyl arenesulfonates can be reduced readily to the corresponding arenethiols quantitatively by treatment with a mixture of triphenylphosphine and a catalytic amount of iodine, while alkanesulfonic acids, sulfinic acids, disulfides, thiosulfonic testers, and sulfonates are also readily reduced to the corresponding thiols similarly. Upon treatment with a mixture of triphenylphosphine and excess iodine, however, these aliphatic sulfur compounds are converted eventually to the corresponding alkyl iodides. The relative reactivities of these sulfonyl derivatives in the reaction with the triphenylphosphine–iodine system are the following. Aromatic series: ArSO2Cl, ArSO2SAr′>ArSO2H>ArSO3R>ArSO3−HNBu3+ (or PyH+)>ArSO3H>ArSO2SO2Ar>>ArSO2CH2C(CH3)3, ArSO3Ar′. Aliphatic series: RSO2Cl, RSO2SR′, RSO2−HNBu3+>RSO3−HNBu3+>RSSR, RSO2H>RSO3H>RSH>RSO3R′. In these reactions, the arenesulfonic acids bearing electron-donating substituents can be reduced more readily than those having electron-withdrawing substituents.
Published Version (
Free)
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
