Tin heterocycles some phenoxastannin and phenothiastannin derivatives

• Published in: Journal of organometallic chemistry Vol. 10; no. 2; pp. 269 - 278
• Main Authors: Kupchik, Eugene J., Ursino, Joseph A., Boudjouk, Philip R.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 1967
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/S0022-328X(00)93086-9

10,10-Dialkylphenoxastannins, the first examples of heterocycles containing the CSnC linkage and oxygen in the ring, were obtained in low yield from the reaction of 2,2′-dilithiodiphenyl ether (I) with dialkyltin dichlorides and, in higher yield, from the reaction of 10,10-dichlorophenoxastannin (III) with organolithium reagents or Grignard reagents. 10,10-Diphenylphenoxastannin could only be obtained by the organolithium and Grignard route. (III) was prepared in high yield by allowing 10,10′-spirobiphenoxastannin (II) to react with stannic chloride. The reaction of (I) with stannic chloride gave three products: (II), tetrakis( o-phenoxyphenyl)tin, and a novel twelve-membered ring heterocycle containing two tin atoms in the ring (VIII). The reaction of (VIII) with stannic chloride gave a high yield of (III). The first examples of heterocycles containing the CSnC linkage and sulfur in the ring were obtained by allowing 2,2′-dilithiodiphenyl sulfone to react with diorganotin dichlorides and stannic chloride. Infrared, far infrared, ultraviolet, and NMR data are reported for the new heterocycles.