The fragmentation of ionized alkyl phenyl ethers

✍ Scribed by Marcia C. Blanchette; John L. Holmes; F. P. Lossing

• Publisher: John Wiley and Sons
• Year: 1989
• Tongue: English
• Weight: 714 KB
• Volume: 24
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/oms.1210240826

✦ Synopsis

The energetics of olefin loss from ionized alkyl phenyl ethers have been determined by ionization and appearance energy measurements. It is concluded that the reaction is governed by one or more of three features: (i) the strength of the bond between the phenoxy radical and the alkyl ion; (ii) the ease of isomerization of the alkyl ions, chiefly by H-shifts therein, and (ii) the strength of the C-H bond (primary, secondary and tertiary) involved in the H transfer to oxygen which precedes the olefin loss. The possible participation in the reaction of distonic ions and proton bound radical-molecule pairs is also discussed. E ~, , ~~ CH,CH3 694 950 982 256 198 CH,CH,CH, 667 929 958 262 172 CH ,CH ,CH,CH , 639 897 942 258 161 CHzCH (CH 3) z 631 880 938 249 123 CH(CH3)CH2CH, 625 81 4 930 179 117 From Ref. 21. C(CH3)3 61 3 742 91 4 129 90 bThe measured energy of the olefin loss relative to the AHf molecular ion.