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Baldwin's rulesBaldwin's Rules in organic chemistry are a series of guidelines outlining the relative favourabilities of ring closure reactions in alicyclic compounds. They were first proposed by Jack Baldwin in 1976 [1] [2].
The rules classify ring closures in three ways:
Additional recommended knowledgeThus, a ring closure reaction could be classified as, eg. 5-exo-trig. It should be noted that 5-endo-trig is disfavoured, but look "nice" on the paper:
Baldwin discovered that orbital overlap requirements for the formation of bonds favour only certain combinations of ring size and the exo/endo/dig/trig/tet parameters. It should be noted that Baldwin's rules are general guidelines, and that exceptions do occur. Eg. cations often disobey Baldwin's rules, and reactions where a second-row atom are included in the ring. The Baldwin disfavoured ring closures and Baldwin favoured ring closures: are listed below.
ExamplesIn one study seven-membered rings are constructed in a tandem 5-exo-dig addition reaction / Claisen rearrangement [3]:
References
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Baldwin's_rules". A list of authors is available in Wikipedia. |