The structure and mechanism of formation of C5H9O+ from ionized phytyl methyl ether
UNSPECIFIED. (1996) The structure and mechanism of formation of C5H9O+ from ionized phytyl methyl ether. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 7 (2). pp. 205-208. ISSN 1044-0305Full text not available from this repository.
The recent proposal that ionized phytyl methyl ether [C16H33(CH3)C = CHCH2OCH3+.] undergoes an allylic rearrangement to ionized isophytyl methyl ether [CH2 = CHC(C16H33)(CH3)OCH3+.] before elimination of an alkyl radical is discussed. Both literature precedent and new results in which the structure of the [M - C16H33.](+) fragment ion is established by comparison of its collision-induced dissociation mass spectrum with the spectra of isomeric C5H9O+ ions of known structure are inconsistent with this proposal. The formation of CH3CH=CHCH=O+CH3 by loss of a gamma-alkyl substituent without Skeletal isomerization rather than CH2=CHC(CH3)=O+CH3 after allylic rearrangement is ex plained in terms of a mechanism that involves two 1,2-H shifts, followed by sigma-cleavage of the resultant ionized enol ether, C16H33(CH3)CH-CH = CHOCH3+..
|Item Type:||Journal Article|
|Subjects:||Q Science > QD Chemistry
Q Science > QC Physics
|Journal or Publication Title:||JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY|
|Publisher:||ELSEVIER SCIENCE INC|
|Number of Pages:||4|
|Page Range:||pp. 205-208|
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