10. Addition Reactions
Hydroboration
5:40 minutes
Problem 8.71c
Textbook Question
Textbook Question8.71 (•••) FROM THE LITERATURE Predict the product of each of the following hydroboration–oxidation or oxymercuration–reduction reactions used in the modern synthetic organic chemistry literature (modified to use reagents we are used to seeing). [These molecules, while perhaps more complex than any you have seen previously, are, in the presence of borane or mercury(II) acetate, simply alkenes. Thus, don't get distracted by the other functional groups and abbreviations present and predict the product based on what you have learned here in Chapter 8.]
(c) A similar sequence was featured in the synthesis of muricadienin, a proposed precursor in the biosynthesis of solamin (Org. Lett. 2014, 16, 5886–5889).
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