78845-11-1Relevant articles and documents
MACROEXPANSION METHODOLOGY: AN EFFICIENT EIGHT UNIT RING EXPANSION
Wender, Paul A.,Sieburth, Scott McN.
, p. 2471 - 2474 (1981)
An efficient eight unit expansion method which is postulated to proceed by either a or consecutive sigmatropic shifts is described.
MACROEXPANSION METHODOLOGY; MEDIUM RING SYNTHESIS BASED ON AN EIGHT UNIT RING EXPANSION PROCESS
Wender, Paul A.,Sieburth McN., Scott,Petraitis, Joseph J.,Singh, Sunil K.
, p. 3967 - 3975 (2007/10/02)
Treatment of 1,2-(E,E)-di(1-buta-1,3-dienyl)cyclohexanol (21) with potassium hydride in tetrahydrofuran at room temperature resulted in the facile formation of a 14-membered ring dienolate which on kinetic protonation provided cyclotetradeca-3,5,7-trien-1-one.This novel rearrangement which provides the basis for an efficient, eight unit ring expansion method was also observed when 5,8-dimethyl-5-hydroxy-1,3,7,9-decapentaene (28), the acyclic analogue of 21, was treatad with potassium hydride in tetrahydrofuran.Methodology for the preparation of 21 and 28 including the preparation of 1-lithio-1,3-butadiene is also described.
