51010-55-0Relevant academic research and scientific papers
REINTERPRETATION OF LONG-RANGE 1H-19F SPIN-SPIN COUPLING IN 1,4-DIHYDRO-1,4-EPOXYNAPHTHTLENES AND RELATED SYSTEMS
Gribble, Gordon W.,Kelly, William J.
, p. 2475 - 2478 (1981)
The long-range 1H-19F coupling reported earlier for the bridgehead proton(s) in 1,4-dihydro-1,4-epoxynaphthalenes (e.g., 1) is shown unequivocally to involve the distal fluorine by a five-bond zig-zag coupling pathway.
UNEXPECTED REGIOSELECTIVE DIELS-ALDER CYCLOADDITION REACTIONS BETWEEN 3-FLUOROBENZYNE AND 2-ALKYLFURANS
Gribble, Gordon W.,Keavy, Daniel J.,Branz, Stephen E.,Kelly, William J.,Pals, Mark A.
, p. 6227 - 6230 (2007/10/02)
The Diels-Alder reaction between 3-fluorobenzyne (1) and 2-alkylfurans (2) gives a mixture of syn adduct 3 and anti adduct 4.The syn cycloadduct invariably predominates and the regioselectivity increases in the order: R= Me Et i-Pr t-Bu, to a maximum of 90percent syn adduct 3d for 2-tert-butylfuran.These results are rationalized in terms of a concerted nonsynchronous transition state that reflects an alkyl steric effect and a polarized aryne 1.
