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Tolman's rule states that, in certain chemical reactions, the steps involve exclusively intermediates of 18- and 16-electron configuration. The rule is an extension of the 18-electron rule. This rule was proposed by American chemist Chadwick A. Tolman. However, there are exceptions to Tolman's rule, even for reactions that proceed via 2e− steps, because many reactions involve intermediates with fewer than 16 electrons.
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