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Featuring a little how-to guide on how I solve mechanism problems! When I was in graduate school, we started each weekly group meeting with a mechanism problem (this is the origin of #mechanismmonday - I used to post those on the group Twitter when I ran it!) The May group did a lot of different types of chemistry - I worked on organocatalyzed conjugate additions, but we also had hardcore organometallic projects and even some electrochem. The mechanisms people brought were always quite varied and very fun.
This is from "Total Synthesis of (−)-Colombiasin A and (−)-Elisapterosin B" published in Angewandte in 2005. Hope you have a great week! From Advanced Problems in Organic Reaction Mechanisms (Problem 55). A fun challenge to get two products from the same reaction conditions!
Today's mechanism is from the book "Advanced Problems in Organic Reaction Mechanisms" shared last week by Victor Kiryak on Twitter!
From the total synthesis of longifolene. Interesting contradiction of violating Bredt's rule, but the cation being stabilized by the double bond. Further discussion of stabilization can be found on LibreTexts. The screenshot RE: Bredt's Rule is from
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Mechanism MondaysA new organic chemistry mechanism each Monday, with the answer posted a few hours later. Archives
January 2024
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