The tertiary amino effect in heterocyclic synthesis : mechanistic and computational study of the formation of six-membered rings

✍ Scribed by L.C. Groenen; W. Verboom; W.H.N. Nijhuis; D.N. Reinhoudt; G.J. Van Hummel; D. Feil

• Book ID: 104203767
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 709 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86166-4

✦ Synopsis

The mechanism of the ring closure of [2-(l-yrmlidinyl)phcnylmcthylene]-(3a) has been studied by kin& pts lo[&JquinoliBc-4,4diarbonitril~

shown that the ratcdctaminin experimental (X-ray) moleculrr auucmrc of2.#srcinfairlygo&grcemcnrInthegnXlnd state geometry a 1.5 hydrogen tratufez will most likely take rotation of the former vinyl gnntp andC-Gbofbd furmat@ &z supraf&#lly. subequalt also take place in a stereochcmically defined way. gtorsbcenlbaairing, Tertiuy~thatkPrmorthosubstiWcntcoaaininOan-boldcurbcuKdtosyn~nitrogencon~ hctaucycler. 'Ihe reactions of tbcsc t&ary aniline& have been w under the name "rur-amino effect andhrvcbeennviewedanumkrdyernlrOobyMethCohnudS~aLy.tInthirrevicwnrctionsof