- N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley-Griffith (TPAP) tandem oxidation-Wittig reactions
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N,N,N′,N′-Tetramethylethylenediamine dioxide (TMEDAO2) was explored as a more atom economical co-oxidant for the Ley-Griffith oxidation of alcohols to aldehydes. TMEDAO2 was found to selectivity oxidise benzylic and allylic alcohols in comparable yields to that of the standard Ley-Griffith co-oxidant (NMO). Importantly TMEDAO2 facilitated tandem Ley-Griffith-Wittig reactions with stabilised ylides, in good to excellent yields, without the requirement of anhydrous conditions.
- Read, Christopher D. G.,Moore, Peter W.,Williams, Craig M.
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supporting information
p. 4537 - 4540
(2015/09/15)
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- Synthesis and reactions of organic compounds with a nitrogen atom. Part XV. Reactions of (+)-3-chloro-2(10)-pinene and (-)-10-chloro-2-pinene with phenyltelluro- and phenylselenosodium
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Toluenesulfonamidation of (+)-3-chloro-2(10)-pinene (4) and (-)-10-chloro-2-pinene (5) with phenylselenosodium (2) or phenyltellurosodium (3) and chloramine-T gave exclusively N-trans-[2′(10′) pinen-3′-yl]toluenesulfonamide (7). Oxidation of 10-phenylseleno-2-pinene (6) and 10-phenyltelluro-2-pinene (12) prepared from the chlorides 4 and 5 was examined. The reduction of toluenesulfonamide 7 with sodium in liquid ammonia gave (+)-trans-3-amino-2(10)-pinene (8).
- Uzarewicz,Scianowski,Bakowska-Janiszewska
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p. 1791 - 1796
(2007/10/03)
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- Hydroboration. 90. Synthesis of 2-isobutyl- and 2-Isopropylapopinenes. Rates and Stoichiometry of the Hydroboration of 2-Organylapopinenes with Borane-Methyl Sulfide and Borane-Tetrahydrofuran
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Two higher analogues of α-pinene, 2-isobutyl- and 2-isopropylapopinenes, promising chiral auxiliaries for asymmetric hydroboration, were readily synthesized from α-pinene in good chemical yield.A quantitative study was made of the rates and stoichiometry of the hydroboration of a number of representative 2-organylapopinenes (2-R-apopinenes) with representative boranes, such as BH3*SMe2 (BMS) and BH3*THF, in order to develop a convenient procedure for the synthesis of mono- and bis(2-organylapoisopinocampheyl)boranes , under investigation as possible improved asymmetric hydroborating reagents.It was evident that the sterically bulkier 2-R-apopinenes such as 2-phenyl- and 2-isopropylapopinenes reacted with boranes at room temperature to form essentially RapBH2 in >/=95percent yield, while a yield of >/=90percent was realized in the case of 2-isobutylapopinene.However, α-pinene, and 2-ethyl- and 2-n-propylapopinenes smoothly reacted with boranes to form a mixture of RapBH2 and Rap2BH.Under the reaction conditions employed, 2-ethyl-, 2-n-propyl-, 2-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes failed to produce clean Rap2BH.The rate of hydroboration decreased significantly with increase in bulk of the organyl group at the 2-position of the apopinene.
- Brown, Herbert C.,Dhokte, Ulhas P.
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p. 2025 - 2032
(2007/10/02)
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