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Beilstein J. Org. Chem. 2019, 15, 497–505, doi:10.3762/bjoc.15.43
Graphical Abstract
Scheme 1: Synthesis of 2-unsubstituted imidazole N-oxides 1 from α-hydroxyiminoketones 2 and formaldimines 3.
Scheme 2: Preparation of adamantyloxyamine (4) and its conversion into N-(adamantyloxy)formaldimine (6a); Ad ...
Scheme 3: Synthesis of 1-(adamantyloxy)imidazole 3-oxides 7a–e and 1-adamantylimidazole 3-oxides 7f,g in acet...
Scheme 4: Deoxygenation of 1-(adamantyloxy)imidazole 3-oxides 7a–d and isomerization of 7b into imidazole-2-o...
Scheme 5: Conversions of imidazole 3-oxides 7a–d into 1-(adamantyloxy)imidazole-2-thiones 10a–d via sulfur tr...
Scheme 6: Syntheses of the non-symmetric 1,3-dialkoxyimidazolium bromides 13a–c and 1-alkyl-3-alkoxyimidazoli...
Scheme 7: Attempted O-adamantylation of imidazole N-oxide 7a with adamantan-1-yl trifluoroacetate and subsequ...
Scheme 8: Synthesis of the symmetric 1,3-di(adamantyloxy)imidazolium bromide (15) and its transformation to 1...
Beilstein J. Org. Chem. 2018, 14, 3076–3077, doi:10.3762/bjoc.14.286
Figure 1: Dispersion = attractive part of the van-der-Waals potential.
Beilstein J. Org. Chem. 2010, 6, 1061–1069, doi:10.3762/bjoc.6.121
Scheme 1: Unimolecular reactivity of hydroxycarbenes under cryogenic conditions: [1,2]H-Tunneling of 1 and 3 (...
Scheme 2: A selection of heterocarbenes that undergo intramolecular C–H insertions.
Scheme 3: Attempted generation of 5 and d-5 as well as their corresponding insertion products.
Scheme 4: Proposed mechanism for the generation of 8 and 9. The [1,2]H-tunneling process apparently cannot co...
Figure 1: Unmodified matrix IR spectrum (Ar, 11 K) of the pyrolysis (600 °C) of 5. Traces of 9 are indicated ...
Figure 2: Unmodified matrix IR spectrum (Ar, 11 K) of the pyrolysis (600 °C) of d-5. Traces of 9 are indicate...
Scheme 5: Decay of the 2,3-dihydrobenzofuran-3-ol molecular radical cation (8+•).
Scheme 6: Attempted generation of 12 and the actual pyrolysis product 11.
Scheme 7: Unanticipated reaction of 6 upon heating in xylenes.
Scheme 8: Potential energy hypersurface of (o-methoxyphenyl)hydroxycarbene (5) (not drawn to scale; ZPVE incl...
Scheme 9: Acid-catalyzed generation of 7 by unreacted 6.