
TY  - JOUR
A1  - Warrener, RN 
A1  - Pitt, IG 
A1  - Russell, RA 
T1  - The Adducts of Isobenzofuran and <I>cis</I>-3,4-Dichlorocyclobutene, and Their Conversion Into Formal Dewar Furan Adducts
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1992
VL  - 45
IS  - 6
SP  - 1035
EP  - 1044
KW  - 
UR  - https://doi.org/10.1071/CH9921035 
N2  - cis-3,4-Dichlorocyclobutene (19) reacts with isobenzofuran (4) to produce three of four possible [ &#960;;45+&#960; 28] cycloaddition products. The isomer (27) is the dominant cycloadduct , which indicates that significant stabilization by the chlorine atoms with isobenzofuran occurs in the transition state leading to this product. Both adducts (26) and (27) are dechlorinated to form the exo  cyclobutene (31), and the other adduct, the isomer (28), yields the endo cyclobutene (33); these products correspond to the formal adducts of cyclobutadiene with isobenzofuran . Separate reactions of cyclobutenes (31) and (33) with 3-chloroperbenzoic acid produce a single anti epoxide in each case, (32) and (34), respectively; these products are identical with the pair of isobenzofuran adducts derived from Dewar furan itself, as reported elsewhere. 
ER  -

