142294-73-3

Upstream product

• 124-38-9 carbon dioxide 
• 143142-53-4 4-bromo-2,6-dimethyl-N-(2,2,5,5-tetramethylcyclopentylidene)aniline 
• 85385-01-9 N-(2,6-dimethylphenyl)cyclopentylideneimine 
• 74-88-4 methyl iodide 

Downstream Products

• 143142-53-4 4-bromo-2,6-dimethyl-N-(2,2,5,5-tetramethylcyclopentylidene)aniline 
• 143142-55-6 2,6-dimethyl-4-nitro-N-(2,2,5,5-tetramethylcyclopentylidene)aniline 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 143142-54-5 3,5-dimethyl-4-<(2,2,5,5-tetramethylcyclopentylidene)amino>aniline 

Relevant academic research and scientific papers

(E/Z) Equilibria, 16. Lone Electron Pair Donor Quality of the Imino Function: Synthesis and Reactivity of Sterically Strongly Congested Iminocyclopentanes

2,6-Dimethyl-N-(2,2,5,5-tetramethylcyclopentylidene)aniline (4h) is obtained by permethylation; it forms salts (5) by N-protonation.Its CN double bond is strongly shielded against nucleophilic attack and cannot be hydrolyzed.Nitration and bromination occur smoothly in the aromatic p-position (12, 13), showing the directing power of the lone electron pair of the imino function.This ?-donor quality is assessed by probing weaker electrophiles and by qualitative competition experiments. Key Words: Imines / Permethylation / Substitution, electrophilic aromatic / Steric shielding

Sterically Congested Molecules, 6. Lone Electron Pair Donor Quality of the Imino Function: Increased Front Strain and Electronic Substituent Effects on Sterically Accelerated Nitrogen Inversion in Iminocyclopentanes

The p-substituents of 2,6-dimethyl-N-(2,2,5,5-tetramethylcyclopentylidene)anilines are modified without interfering reactions at the CN double bond.The resultant series (5-8, 10-19) shows a strong (ca. -4.7 kcal/mol) steric acceleration of (E/Z) diastereo