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Title: On the road to stable, isolable [4]cumulenes: Reactivity and cyclization reactions
Abstract

The design and synthesis of persistent tetraaryl[4]cumulenes are reported. Derivatives with phenyl endgroups ([4]Phand[4]Ph/Ar*) are susceptible to reactions during synthesis and/or purification that complicate isolation of the desired product, particularly intermolecular dimerization reactions. Incorporation of (3,5‐di‐tert‐butyl)phenyl endgroups (Ar*) provides increased stability, culminating in the stable and isolable [4]cumulene[4]Ar*. Cumulene[4]Ar*remains, however, susceptible to dimerization under pressing conditions, and[4]Ar*also readily reacts with electrophiles under mild conditions that lead to intramolecular cyclization. Given the structural complexity of the side products in these studies (compounds3,10,14,17,18), X‐ray crystallography plays a vital role in their identification.

 
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Award ID(s):
2003411
NSF-PAR ID:
10376730
Author(s) / Creator(s):
 ;  ;  ;  ;  ;  ;  ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Journal of Physical Organic Chemistry
Volume:
36
Issue:
2
ISSN:
0894-3230
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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