1-Naphthalenethiol Explained

1-Naphthalenethiol is an organosulfur compound with the formula C₁₀H₇SH. It is a white solid. It is one of two monothiols of naphthalene, the other being 2-naphthalenethiol.

Synthesis

A practical synthesis involves the tin/HCl-reduction of the naphthalene-1-sulfonyl chloride.^[1] 1-Naphthalenethiol can also be prepared from 1-bromonaphthalene by Pd-catalyzed reaction with the silylthiolate ⁱPr₃SiSK followed by hydrolysis of the silathioether.^[2] It was first prepared from the Grignard reagent generated from 1-bromonaphthalene. Treatment of that reagent with elemental sulfur followed by acidification gave the compound.^[3] It has been produced by the iodine-catalyzed reduction of 1-naphthalenesulfonic acid with triphenylphosphine.^[4]

Reactions

Treating 1-naphthalenethiol with butyl lithium in the presence of tmeda affords the 2-lithio derivative.^[1]

Notes and References

1. 10.1139/v98-230. A versatile synthetic route to 1,5-dithiocins from o-mercapto aromatic aldehydes. 1999. Still. Ian WJ. Natividad-Preyra. Rosanne. Toste. F Dean. Canadian Journal of Chemistry. 77. 113–121.
2. Potassium Triisopropylsilanethiolate: Vinyl and Aryl Sulfides Through Pd-Catalyzed Cross Coupling. Rane. Anil M.. Miranda. Edgar I.. Soderquist. John A.. Tetrahed. Lett. . 1994. 35. 20. 3225–6. 10.1016/S0040-4039(00)76870-5.
3. Contribution to the Study of Sulphur and Selenium Compounds of the Aromatic Series. Taboury, F.. Annales de Chimie et de Physique. 1908. 15. 5–66.
4. Reduction of Sulfonic Acids and Related Organosulfur Compounds with the Triphenylphosphine-Iodine System. Oae Shigeru. Togo Hideo. Bulletin of the Chemical Society of Japan. 1983. 56. 12. 3801–3812. 10.1246/bcsj.56.3802.