Free radical chlorination of bicyclo[2.1.0]pentane

✍ Scribed by Robert S. Boikess; Mary D. Mackay

• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 176 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70774-x

✦ Synopsis

Reaction of chlorine with bicyclo[2.l.Olpentane in chloroform at -2pC has been reported to occur by electrophilic addition to the three membered ring leading to a 1,3-chloronium ion and to give predominantly dichlorides (1). Free radical chlorinations of several strained bicyolic systems (2) have been reported to occur primarily without rupture of the bioyclic ring systems.

We have investigated the chlorination of bicyclo[2.l.O~pentane end wish to report on the novel course of this reaction.

Bioyclo[2.l.O]pentane, free of cyclopentene, was prepared by the method of Criegee (3) and was photochlorinated in a modification of the vapor phase chlorination apparatus described by Roberts and Masur (b). The hydrocarbon vapors were boiled up through a pyrex spiral irradiated with two Sylvania 275 watt sunlamps, where they were mixed with chlorine, which was added slowly so that there was always a large excess of substrate to chlorine. The vapors.were then condensed