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Ion cyclotron resonance studies of ambident nucleophiles. The reactions of the trimethylsilyl cation with alkenyl ethers and alkoxy ketones
Author(s) -
Dottore Marie F.,
Trenerry V. Craige,
Stone David J. M.,
Bowie John H.
Publication year - 1981
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.1210160804
Subject(s) - chemistry , alkoxy group , ether , adduct , trimethylsilyl , substituent , medicinal chemistry , nucleophile , fragmentation (computing) , alkoxide , ion cyclotron resonance , photochemistry , organic chemistry , ion , alkyl , catalysis , cyclotron , computer science , operating system
Abstract Alkenyl ethers react through oxygen with Me 3 Si + to yield intermediates which undergo characteristic fragmentations. In the particular case of allyl ethers, the decomposing adduct undergoes several fragmentations through the allyl substituent via 6‐membered transition states. The reaction between Me 3 Si + and alkoxy carbonyl derivatives yields both ‘ether’ and ‘keto’ adducts, characterized by their fragmentation patterns. The ‘ether’ adducts formed from Me 3 Si + and alkoxy acetones undergo the same basic eliminations as those observed for the allyl ether/Me 3 Si + systems.