85366-27-4Relevant academic research and scientific papers
REGIO- AND STEREO-CHEMICAL FEATURES OF THE STANNYLCOPPER(I)-INDUCED SUBSTITUTION IN PROPARGYLIC SUBSTRATES
Ruitenberg, K.,Westmijze, H.,Meijer, J.,Elsevier, C. J.,Vermeer, P.
, p. 417 - 422 (2007/10/02)
Stannylcopper(I) species, R3SnCu and 2CuLi, preferentially convert propargylic substrates, R1CCCR2R3X (X=Br, MeCO2, MeS(O)O or MeSO3) into allenes R3Sn(R1)C=C=CR2R3.Only when the group R1 causes much greater steric hindrance than with R2 and R3 is the acetylenic product R1CCCR2R3SnR3 formed.The stereochemical course of the allene formation has been studied in both the steroid and non-steroid series, and found to be mainly or exclusively anti.
