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Search for "silylene" in Full Text gives 5 result(s) in Beilstein Journal of Organic Chemistry.
Two-fold addition reaction of silylene to C60: structural and electronic properties of a bis-adduct
Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100
- 305-8577, Japan 10.3762/bjoc.20.100 Abstract The addition reaction of C60 with silylene 1, a silicon analog of carbene, yielded the corresponding bis-adduct 3. The structure of 3 was determined by single-crystal X-ray structure analysis, representing the first example of a crystal structure of a
- . Keywords: bis-adduct; C60; fullerene; silirane; silylene; Introduction The chemical functionalization of fullerenes has been exploited extensively from both fundamental and practical perspectives, elucidating their potential applications for biochemistry, nanomaterials sciences, and molecular electronics
- Figure 1 [5]. Diederich and co-workers developed a general methodology using tether-directed remote functionalization for the regioselective formation of multiple adducts of fullerenes [6]. In our earlier reports, the reactions of C60 and C70, with silylene Dip2Si (1, Dip = 2,6-diisopropylphenyl), a
Unexpected loss of stereoselectivity in glycosylation reactions during the synthesis of chondroitin sulfate oligosaccharides
Beilstein J. Org. Chem. 2019, 15, 137–144, doi:10.3762/bjoc.15.14
- group was the key for the high efficiency of this coupling. Similarly, condensation between peracylated GlcA donor 3 and 4 gave disaccharide 5 in excellent 97% yield (Scheme 2). The cyclic silylene group was then replaced by two acetyl groups because it is well-known that cyclic protecting groups at
Silyl-protective groups influencing the reactivity and selectivity in glycosylations
Beilstein J. Org. Chem. 2017, 13, 93–105, doi:10.3762/bjoc.13.12
- silylene protective groups are also becoming increasingly popular. In carbohydrate chemistry silyl protective groups have frequently been used primarily as an orthogonal protective group to the more commonly used acyl and benzyl protective groups. However, silyl protective groups have significantly
- -controlled glucuronylation, where the bulky silylene in 75 ensures high selectivity without neighboring group participation (Scheme 16) [67]. Conclusion Much indicates that glycosyl donors with silyl protective groups generally are more reactive than their alkylated counterparts presumably due to the O-silyl
Metal–ligand multiple bonds as frustrated Lewis pairs for C–H functionalization
Beilstein J. Org. Chem. 2012, 8, 1554–1563, doi:10.3762/bjoc.8.177
- Schrock [15][16]. The reverse Mδ−═Eδ+ case, in which π backbonding from an electron-rich metal into a relatively electropositive ligand is insufficient to fully attenuate the basicity of the metal and/or the π acidity of the ligand (Figure 1b), is encountered for low-oxidation-state late-metal silylene
- silylenes [54][55], insertion of olefins into hydrosilylenes [56], and bimolecular redistribution of thiolates between ruthenium silyl and silylene complexes [57]. Reactivity that involves metal-ligand cooperation (in the sense described in this article) has been reported in the formal [2 + 2] cycloaddition
- of isocyanates to ruthenium(II) silylenes [58] (Scheme 8). These complexes do not react with nonpolar substrates (although a possible cycloaddition with azobenzene was reported), and the overall cycloaddition was found to proceed through initial nucleophilic attack at an electrophilic silylene
Dependency of the regio- and stereoselectivity of intramolecular, ring-closing glycosylations upon the ring size
Beilstein J. Org. Chem. 2011, 7, 1609–1619, doi:10.3762/bjoc.7.189
- leaving group [5][6][7][8][9]. In the “aglycon-delivery concept”, the glycosyl acceptor is attached to a labile acetal [10][11][12][13][14] or silylene group [15][16][17], which is cleaved and the glycosyl acceptor is “delivered” to the anomeric center upon its activation. In the “prearranged-glycoside
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