A facile and efficient synthesis of medium rings via a bicyclic sulfonium ion was developed. Spectroscopic evidence for the formation of an intermediate sulfonium moiety is provided. The sulfur atom served as a "bridge" to access the medium ring system and could be removed after use via a Ramberg-Backlund process. As a result of the readily available starting materials, simple operation, and mild conditions, these reactions should be an appealing strategy in organic synthesis.
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