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Interaction and rearrangement of trimethylsilyloxy functional groups. The structural significance of the m/e 147 ion in the mass spectra of trimethylsil steroidal ethers
Author(s) -
Sloan Sharon,
Harvey D. J.,
Vouros Paul
Publication year - 1971
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210050705
Subject(s) - chemistry , steric effects , trimethylsilyl , cleavage (geology) , stereochemistry , mass spectrum , ion , ring (chemistry) , medicinal chemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
Requirements for trimethylsilyloxy group interaction and rearrangement are discussed. It is evident that formation of the m/e 147 ion is a function of the stereochemistry, steric hindrance and separation of the trimethylsilyloxy groups and reflects the stereochemistry of the steroid itself. It is postulated that ring cleavage is not necessarily a prerequisite for the formation of this ion. The occurrence of the m/e 147 ion can be structurally informative in trimethylsilyl derivatives of steroidal alcohols.