Free-radical halogenation of 1-aza-adamantane

✍ Scribed by W.N. Speckamp; A.W.J.D. Dekkers

• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 182 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93153-3

✦ Synopsis

Although radical reactions of tertiary amines have been postulated to play an essential role in certain biological processes2 only scarce &endcal information is available3 on this type of reaction. Aiming at novel routes to 3-halogenated 1-aza-adamantanes we have investigated the reaction of la with different halogenating agents.

Irradiation4 of 2 in presence of BrCC13 immediately resulted in the formation of a white precipitate: the sams product 2 was obtained on reaction of 1 with BrCC13 in presence .of Bz202. As micro analysis of 2 revealed the presence of both Cl* 0 and Br the reaction was repeated with Ccl4 as halogen source.

Again a crystalline compound was formed in a yield of 81% based upon converted la _, which on the basis of its analytical data was formulated as the dimei 1, (x = cl ) q >300°c (aec)'. The latter product was also formed upon photochlorination of la with CC13S02C1 (yield 64%).