✍ Scribed by R. H. Hall; S. Harkema; H. J. den Hertog; G. J. van Hummel; D. N. Reinhoudt
No coin nor oath required. For personal study only.
2‐Butynedinitrile reacts by (2 + 4)‐cycloaddition with one or two equivalents of 2,3,4,5‐tetramethylfuran to give 1,4,5,6‐tetramethyl‐7‐oxabicyclo[2.2.1]hepta‐2,5‐diene‐2,3‐dicarbonitrile (1) and 1α,4α,4aα, 5β,8β,8aα‐hexahydro‐1,2,3,4,5,6,7,8‐octamethyl‐1,4:5,8‐diepoxy‐naphthalene‐4a,8a‐dicarbonitrile (5), respectively. The presence of aluminium(III) chloride has no effect on the reactions, unlike the corresponding reaction with the analogous thiophene. On irradiation, 1 is converted into 2,4,6,7‐tetramethyl‐3‐oxatetracyclo[3.2.0.0^2,7^.0^4,6^]heptane‐1,5‐dicarbonitrile (2) in good yield. The structure of 5 has been determined by a single‐crystal X‐ray analysis.
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## Abstract magnified image The regiochemistry was investigated for the reaction of 2‐chloromethyl‐4,5‐dichloropyridazin‐3(2__H__)‐one (**1****)** with some phenols **2** in the presence of a base in organic solvents. Seven diphenoxy derivatives **5** were synthesized selectively from **1** and ph