A synthesis of analogues of Kagan's ether 7a is reported. The procedure has reasonable generality and promises to be important in the synthesis of molecular clefts. The final step consists of an electrophilic attack of an oxonium ion on an aromatic ring, and aromatics substituted with electron-withdrawing groups do not participate in the reaction.Sir: The investigation of molecular cavities capable of binding to as well as inducing reactions of organic substrates is a recognized field of established and growing importance.1 We wish to contribute to this area by preparing and studying a series of molecular clefts that are analogues of 5,6,ll,12-tetrahydro-5,ll-epoxydibenzo[o,e]cyclooctene (Kagan's ether, 7a). The parent of this family is represented by 1. Inspection of Dreiding or CPK models suggests that the terminal phenyl rings of 1 lie in virtually parallel planes and are approximately 7 Á apart. This distance is nearly ideal for binding an aromatic guest or "tweezing" a base pair of DNA.2 While the cleft in 1 is relatively shallow, appropriately constructed congeners should prove interesting as hosts for aromatic guests and DNA bis-intercalators.3 In this paper we report some of the synthetic methodology we have developed to pursue these goals.
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