Small ring compound XIV formolysis of (1,2-epoxy-1-cyclopropylethyl)-benzene

✍ Scribed by Tatsuya Shono; Ikuzo Nishiguchi; Akira Oku; Ryohei Oda

• Book ID: 104223680
• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 180 KB
• Volume: 8
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)90540-9

✦ Synopsis

The unusual stability o? the oyolopropyloarbonIu Ion has been studied In many reoent works. (1) The aoid oatalyzed ring opening of unsjmmetrloally substituted epoxldes In Ionizing media has been thought to have an SN-l-like transltlon state, (2) thus the tormolysls of (1,2-epoxy-l-oyolopropylethyl)-benzene(I), synthesized from ayolopropyl phenyl ketone using the Franzen method(3) (yield 78%. bp 70' at Znuu), was studied with the expeotation that the transition state would Involve a oyolopropyloarbonium Ion.

The solvolysIs (60°, 3hr.) gave the following iour maJor produots, II (bp 61° at 4mm, 2,4-dlnltrophenylhydrazone, mp 137O. Calod. for C1lIileN4041