The following synthesis was developed in an effort to
Chapter 19, Problem 19.93(choose chapter or problem)
The following synthesis was developed in an effort to prepare an analogue of a polycyclic aromatic hydrocarbon in which one of the CRC bonds was replaced with a B!N unit (J. Am. Chem. Soc. 2011, 133, 1861418617). Such derivatives are expected to display unique optical and electrical properties and thus may be useful in the preparation of novel organic electronic materials. N 1) BuLi N BCl2 N B H 1 2 3 AlCl3 2) BCl3 (a) Propose a mechanism for the conversion of compound 1 to compound 3. (b) In compound 3, do you expect each of the six rings to be aromatic, giving one extended aromatic system for the compound? Explain your answer. (c) Analysis of the actual structure of 3 (as well as its hydrocarbon analogue) reveals that the central two rings are slightly twisted (i.e., nonplanar). Provide a rationale for this finding.
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