REACTION OF STANNENES AND PHOSPHАSTАNNENES WITH ALDEHYDES AND KETONES: NEW TIN FOUR-MEMBERED RING DERIVATIVES

Abstract

Stannene Tip₂Sn=СR₂ 1 (Tip = 2,4,6-triisopropylphеnyl, CR₂ = fluorenylidene) enters a [2+2] cycloaddition reaction with benzophenone to afford the four-membered ring derivative 2. This stannaoxetane undergoes a [2+2] decomposition with formation of the corresponding stannanone 8 and alkene 9 and an easy hydrolysis by initial cleavage of the Sn–C bond. Diphenylacetaldehyde also gives with 1 a stannaoxetane, which has been characterized by its hydrolysis products. Phosphastannene Tip₂Sn=PAr 13 (Ar = 2,4,6-tri-tert-butylphenyl) reacts with benzaldehyde according to a [2+2] cycloaddition pattern leading to stannaphosphaoxetane 14, whereas ene-products 19-21 were obtained with acetaldehyde, acetone and acetophenone.

Also published in Chemistry of Heterocyclic Compounds, 1999, 35 (8), pp 965-972

http://link.springer.com/article/10.1007/BF02252165