Utilizing a regioselective hydrogen atom transfer (RHAT) strategy, this study demonstrates a triple RHAT process accompanied by C–O bond homolysis to generate unusual less-conjugated or contra-thermodynamic olefins, a transformation rarely documented in the literature. The key to this conversion is the uncommon RHAT from the secondary ether C–H bond, rather than the weaker tertiary acetal C–H bond. This protocol offers a diverse class of synthetically versatile, less-conjugated, or contra-thermodynamic olefins.

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