- Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
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This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.
- Lee, Melissa,Sanford, Melanie S.
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supporting information
p. 572 - 575
(2017/02/10)
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- Amine-directed hydroboration: Scope and limitations
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Iodine activation induces intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes with good to excellent control of regiochemistry compared to control experiments using excess THF?BH3. Deuterium labeling and other evidence confirm that the iodine-induced hydroboration reaction of homoallylic amine boranes occurs via an intramolecular mechanism equivalent to the classical 4-center process and without competing retro-hydroboration. Longer carbon chain tethers result in lower regioselectivity, whereas the shorter tether in allylic amines results in a switch to dominant intermolecular hydroboration. Regioselectivity in THF?BH3 control experiments is higher for the allylic amine boranes compared to the iodine activation experiments, whereas the reverse is true for homoallylic amine borane activation.
- Scheideman, Matthew,Wang, Guoqiang,Vedejs, Edwin
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supporting information; experimental part
p. 8669 - 8676
(2009/02/03)
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- New routes to diethyl 1-alkenylphosphoramidates
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New routes to N-(diethoxyphosphoryl)imines derived from enolizable carbonyl compounds have been investigated. Three different procedures were studied: (i) the aza-Claisen condensation of ethyl-[N-(diethoxyphosphoryl)]-formimidate with enolizable ketones, (ii) the reaction between diethyl N-sulfinylphosphoramidate and aliphatic aldehydes, and (iii) the thermally induced reaction of diethyl phosphoramidate with ketone diethyl acetals. With two exceptions in all cases the products were identified as diethyl 1-alkenylphosphoramidates with no spectroscopically detectable amounts of imine tautomers. The aza-Claisen condensation can be recommended as a simple and effective route to diethyl 1-alkenyl-3-oxophosphoramidates. (C) 2000 Elsevier Science Ltd.
- Napieraj, Anna,Zawadzki, Stefan,Zwierzak, Andrzej
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p. 6299 - 6305
(2007/10/03)
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- PROTECTION OF PRIMARY AND SECONDARY AMINES IN THE HYDROBORATION REACTION
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Trimethylsilyl groups are efficient to protect the N-H bonds of olefinic amines in the hydroboration reaction with BMS; deprotection is easily run with methanol and affords aminoorganoboranes which can be used without any oxydation.
- Dicko, A.,Montury, M.,Baboulene, M.
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p. 6041 - 6044
(2007/10/02)
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- Pyrazolo[3,4-b]pyridine compounds
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Certain pyrazolo[3,4-b]pyridine compounds which are useful for their activity in the central nervous system of warm-blooded animals, of the following formula (I) STR1 wherein R1 is lower alkyl; Ra is hydrogen and Rb is hydroxy or Ra and Rb combine to form a =O group; R5 is hydrogen or lower alkyl; and R6 is lower alkyl, and the pharmaceutically-acceptable salts thereof.
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- Quaternary alkynoxymethyl amines
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This invention relates to quaternaries of alkynoxymethyl amines and uses thereof. These may be summarized by the following formulae: STR1 where R and R' are substituted groups such as alkyl, aryl, etc.; R'" is an acetylenic group; and X is an anion; and STR2 where R and R'" having the same meaning as in (1) and Z is a bridging group, preferably hydrocarbon such as alkylene, alkinylene, alkenylene, arylene, etc.
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- Microbiocidal quaternaries of halogen derivatives of alkynoxymethyl amines
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This invention relates to quaternaries of halogen derivatives of alkynoxymethyl amines and uses thereof. These may be summarized by the following formulae: STR1 where R and R' are substituted groups such as alkyl, aryl, etc.; R" is an alkylidene group; and X is halogen and A is an anion; and STR2 where R, R' and R" having the same meaning as in (1) and Z is a bridging group, preferably hydrocarbon such as alkylene, alkinylene, alkenylene, arylene, etc.
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- Halogen derivatives of alkynoxymethyl amines
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This invention relates to halogen derivatives of alkynoxymethylamines and to uses thereof. The present invention may be ideally illustrated by the following equation: where R is a substituted group, preferably hydrocarbon, such as alkyl, cycloalkyl, aryl, etc., R' is hydrocarbon, preferably alkylene, and where X is halogen.
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- Alkynoxymethyl amines
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This invention relates to alkynoxymethyl amines, to methods of preparing them, and uses thereof, particularly as corrosion inhibitors. These compounds are prepared by reacting an amine, such as RNH2, with an aldehyde, such as formaldehyde, and an alkynol, such as propargyl alcohol, to yield compounds of the formula where R is a substituted group, preferably alkyl, cycloalkyl, aryl, etc., and R' is an acetylenic alcohol moiety.
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