- NITROSATION REAGENTS AND METHODS
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Provided are compounds that can find use as nitrosation reagents. Provided are nitrosation methods that include reacting a substrate with one of the provided nitrosation reagents and thereby generating a nitrosation product. Provided are kits including a nitrosation reagent. Provided are compositions wherein the nitrosation reagent is enriched in the 15N isotope.
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Paragraph 00152
(2022/02/06)
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- Directed Ortho metalation-cross coupling strategies. N-cumyl arylsulfonamides. Facile deprotection and expedient route to 7- and 4,7-substituted saccharins
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(Chemical Equation Presented) By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a-g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation-carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4).
- Blanchet, Jerome,Macklin, Todd,Ang, Patrick,Metallinos, Costa,Snieckus, Victor
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p. 3199 - 3206
(2008/02/04)
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- N-cumyl benzamide, sulfonamide, and aryl O-carbamate directed metalation groups. Mild hydrolytic lability for facile manipulation of directed ortho metalation derived aromatics
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(Matrix Presented) N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.
- Metallinos, Costa,Nerdinger, Sven,Snieckus, Victor
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p. 1183 - 1186
(2008/02/09)
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- Penultimate group effects in free radical telomerizations of acrylamides
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The telomerization of several acrylamides, most containing chiral auxiliary groups, was investigated. The first-formed stereogenic center in the n = 2 telomer (the penultimate center) has a significant effect on the configuration of the second (ultimate) center in the product. The penultimate chiral center of oxazolidine-derived acrylamides directs the configuration of the ultimate center such that the erythro n = 2 product is preferred. Sultam-substituted acrylamides preferentially lead, on the other hand, to threo products or give products with little stereoselectivity.
- Porter, Ned A.,Carter, Randall L.,Mero, Christopher L.,Roepel, Michael G.,Curran, Dennis P.
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p. 4181 - 4198
(2007/10/03)
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