Organotin compounds

• Published in: Journal of organometallic chemistry Vol. 364; no. 1; pp. 39 - 55
• Main Authors: Podestá, Julio C., Ayala, Alicia D., Chopa, Alicia B., Giagante, Nelda N.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.03.1989
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/0022-328X(89)85329-X

Free radical hydrostannation of methyl 3,4-dihydronaphthalene-1-car☐ylate (I), methyl 3,4-dihydronaphthalene-2-car☐ylate (III), and methyl 1,4-dihydronaphthalene-2-car☐ylate (V) with triorganotin hydrides, R 3SnH (R = Me, n-Bu, Ph) gives the energetically unfavourable cis products, 2-triorganostannyl-1,2,3,4-tetrahydronaphthalene-1-car☐ylate (II), 1-triorganostannyl-1,2,3,4-tetrahydronaphthalene-2-car☐ylate (IV), and 3-triorganostannyl-1,2,3,4-tetrahydronaphthalene-2-car☐ylate (VI) in high yields, via a trans addition of the tin hydrides. The hydride abstractions by the intermediate 2-, 1-, 3-triorganostannyl-1,2,3,4-tetrahydronapththyl radicals (XI, XII and XIII respectively) take place stereospecifically and exclusively from the less-hindered ring side. The structures of the isomers II, IV, and VI, were established by (a) their transformation into the corresponding chlorodiorganostannyl derivatives VIII, IX, and X, which were shown spectroscopically to have cis stereochemistries by intramolecular complexation of the ester group, and (b) their NMR data. Full 1H, 13C, and 119Sn NMR data are given.