Synthesis of 2,6-Hexa-tert-butylterphenyl Derivatives, 2,6-(2,4,6-t-Bu(3)C(6)H(2))(2)C(6)H(3)X, where X = I, Li, OH, SH, N(3), or NH(2)

A "double benzyne" reaction between 1,3-dichloro-2-iodobenzene and 2,4,6-t-Bu(3)C(6)H(2)MgBr followed by the addition of iodine led to 2,6-(2,4,6-t-Bu(3)C(6)H(2))(2)C(6)H(3)I (HTBTI) in 65% yield. Lithiation of HTBTI with Li-t-Bu gave Li(Et(2)O)(2)HTBT from which HTBTSH, HTBTN(3), HTBTNH(2), and HTBTOH were prepared. An X-ray structure of W(OHTBT)(2)Cl(4) shows that the two HTBTO ligands are trans to one another with the t-Bu(3)C(6)H(2) groups on one HTBTO interdigitated with the t-Bu(3)C(6)H(2) groups on the other HTBTO.