Althoughthemultifarious nature of (CH)ioh.ydrocarbcm chemistryhas engenderedmuch recent interest in these molecules, no attention has yet been paid to the stereoelectronic control which benso fusion could exert on the various bond reorganizations characteristic 1
of the parent systems. In this preliminery report, we describe a convenient synthesis of the title cwxpound (k) and provide the first indicatim that mechanistically significant information csn be derived from structural modifications of this type. Addition of benzyne (frcun diazotized anthrenilic acid) to 7,8~ichlarobicyclo[k.2.0]-octaG?,kliene (&)o afforded (4C$ yield) 2 (mp l8l-l&'o)3 and z(mp 134-135')'which were readily separated by alumina chromatography. Treatment of these dichlorides with sodium anthrscene in anhydrous tetrshydrofuran gave k (mp 51-52Β°)3 in quantitative yield. Ihe anti stereochemistry of kfollous from steric considerations,4 energetically favorable secondary orbital intermticns expected in the transition state of the bensyne cycloaddition, and spectral data [Scg3 7.11 (ABBE, 4H, aryl), 6.22 (3 iine~, ZH, vinyl), 6.05 (a, 2xi, cyclobutene vinyl), 3.6-3.9 (m, 2H, n&him), and 2.65 (m, 2Ii, cyclobutene methine)].