Symmetrical and Unsymmetrical Cleavage of Diborane by Amines
In the reaction
the amine(s) is(are)
Options
Topics & Concepts
Step-by-Step Solution
To determine the nature of the amine(s) , we examine the cleavage behavior of diborane () in the presence of Lewis bases.
Diborane undergoes two types of cleavage reactions depending on the steric hindrance and basicity of the attacking Lewis base:
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Symmetrical Cleavage:
Sterically bulky Lewis bases (such as tertiary amines, large phosphines, ethers, and ) cause symmetrical cleavage of the diborane bridge, yielding monomeric Lewis acid-base adducts:
For example, with trimethylamine ():
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Unsymmetrical Cleavage:
Small, less sterically hindered Lewis bases cause unsymmetrical cleavage across the bridging system, generating an ionic salt consisting of a complex cation and a tetrahydroborate anion:
This mode of cleavage occurs with:- Ammonia ()
- Primary amines (e.g., )
- Secondary amines (e.g., )
Since the given reaction:
represents the unsymmetrical cleavage of diborane, the amine must be a sterically unhindered base, which includes , , and . In contrast, is sterically hindered and undergoes symmetrical cleavage.
Therefore, the correct options are A, B, and C.