New Possible Applications of Heavy Main‐Group Elements in Organic Synthesis

Abstract

Abstract Aside from elements of the 2nd row, and one element of the 3rd row of the periodic system—Si, P, S, and Se, respectively, whose organoelement groups such as Me 3 Si and Ph 3 P ⊕ have proven useful in numerous organic syntheses—other elements of the 3rd as well as 4th and 5th row (Ge, As, Sn, Sb, Te, Pb, Bi) can also be used as components of synthetically useful organoelement groups, the elements As, Sn, and Pb, in particular, offering certain advntages over the others. Some of these organoelement groups are suitable equivalents for Li‐ or halogen‐substituents attached to carbon; they stabilize carbanionic centers (minimum of this effect at the 3rd‐row elements), and owing to their suitability as leaving groups in β‐eliminations, also open up interesting synthetic possibilities. The thermally unduced syn ‐ and silica‐gel induced anti ‐elimination of Ph 3 Sn, Ph 2 Sb, Ph 3 Pb, together with β‐OH, are novel. With the newly synthesized compounds Ph n El—Ch 2 —Li (El = Sn, Pb, As, Sb, Bi) and other α‐ and β‐lithiated R n El‐ and Ph 2 As(O)‐reagents such organoelement groups can be introduced into organic compounds and exploited in organic and organoelement synthesis.