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Electron-impact-induced 3,3-sigmatropic rearrangement and cyclization in phenyl allenylmethyl ethers

✍ Scribed by D.V. Ramana; K.K. Balasubramanian; M.S. Sudha; T. Balasubramanian

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
458 KB
Volume
6
Category
Article
ISSN
1044-0305

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✦ Synopsis

A 3,3-sigmatropic rearrangement in the M(+Β·) of phenyl allenylmethyl ether is proposed for the observed losses of CO, C2H4, and CH3. Direct cyclization in the M(+Β·) also leads to the [M-CH3] ion. The presence of sulfur as the heteroatom in phenyl allenylmethyl sulfide does not significantly influence the occurrence of Claisen rearrangement. Ortho interaction of the nitro group with the allenyl double bond in the side chain leads to characteristic fragment ions in 2-nitrophenyl allenylmethyl ether. Linked scans, high-resolution mass spectrometry, collision-activated dissociation-B/E linked-scan spectra, and D-labeling have been employed to support the proposed mechanisms and ion structures.

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## Abstract In view of the current interest in the electron‐impact induced rearrangements of both trimethylsilyl derivatives and bifunctionalized cyclohexanes, the mass spectral properties of several alkoxycyclohexanol trimethylsilyl ethers and alkoxycyclohexyl trimethylsilanes have been investigat