Synthesis of 2-chloroalkyl-1,4-naphthoquinones and their reactivity in the formation of autocomplexes

✍ Scribed by Victor Prezhdo; Oleg Prezhdo; Elena Ovsiankina

• Book ID: 103908359
• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 406 KB
• Volume: 51
• Category: Article
• ISSN: 1386-1425
• DOI: 10.1016/0584-8539(95)01517-5

✦ Synopsis

A series of the chloroalkyl derivatives of 1,4-naphtoquinone were synthesized and the electronic absorption spectra in 200-350 nm of these compounds were studied with the purpose of obtaining autocomplexes. The electronic absorption spectra of 1,4-naphtoquinones are characterized by four z~ ~r* bands which have different sensitivity of 2ma x to the electronic effects of the substituents. Some of the rules of the substituent influence on the spectral characteristics were found. Both steric factors, such as the formation of the cyclic structures due to the local interaction between the chloroethyl and chloropropyl radicals and the carbonyl of the quinone ring, and electronic effects, such as the insufficient delocalization of the extra change in -CH 2 CH~ leading to the poor stability of the carbocation, encumber the course of the reaction of complex formation.