
TY  - JOUR
A1  - Anthony, IJ 
A1  - Wege, D 
T1  - The Synthesis and Reactivity of 5H-Cycloprop[f]isobenzofuran and Related Compounds. A Kinetic Probe for the Mills-Nixon Effect
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 12
SP  - 1263
EP  - 1272
KW  - 
UR  - https://doi.org/10.1071/CH9961263 
N2  - 5H-Cycloprop[f]isobenzofuran (6) and the sulfur analogue 5H-cyclopropa[f][2] benzothiophen (18) have been prepared by a sequence of reactions involving trapping of 1,2-dibromocyclopropene with 3,4-dimethylidenetetrahydrofuran and 3,4-dimethylidenetetrahydrothiophen followed by sequential dehydrogenation and di-dehydrobromination. Both cyclopropa -fused heterocycles, like their parents, have limited stability. Several other 5,6-methylene-bridged and 5,6-disubstituted isobenzofurans (32) have been generated and characterized as their adducts with dimethyl fumarate . Second-order rate constants for the reaction of dimethyl  fumarate with isobenzofuran, 5H-cycloprop[f] isobenzofuran as well as the series of substituted derivatives have been measured. The reactivity span is only one order of magnitude suggesting that &#960;-bond fixation (the Mills-Nixon effect) does not play a significant role in determining the reactivity of (6). 
ER  -

