Steroid rearrangements. Reactions of a 16,17.alpha.-epoxypregnan-20-one with hydrogen fluoride. Thermal dehydrofluorinations

Hoff, Dale R.

doi:10.1021/jo00832a035

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2011

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Cited by 8 publications

(1 citation statement)

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“…25 Several acids, such as TsOH, 26 HF, 27,28 H 2 SO 4 22 have been employed in this transformation. The formation of these epimers has been explained by an acid-catalyzed reversealdol equilibrium involving the 16-hydroxy-20-keto function of the rearranged steroid.…”

Section: Introductionmentioning

confidence: 99%

Bismuth(III) triflate-catalyzed rearrangement of 16α,17α-epoxy-20-oxosteroids. Synthesis and structural elucidation of new 16α-substituted 17α-alkyl-17β-methyl-Δ13-18-norsteroids

et al. 2009

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Section: Introductionmentioning

confidence: 99%

Bismuth(III) triflate-catalyzed rearrangement of 16α,17α-epoxy-20-oxosteroids. Synthesis and structural elucidation of new 16α-substituted 17α-alkyl-17β-methyl-Δ13-18-norsteroids

et al. 2009

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Modern Methods to Prepare Monofluoroaliphatic Compounds

Sharts

Sheppard

2011

Organic Reactions

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Organic fluorine chemistry has been important since the 1930s. The development of fluorine chemistry during World War II is well documented. Fluorine chemistry emerged in the 1950s because of three events: Large‐scale research designed to synthesize fluorine‐containing rockets was initiated. A fluorine atom at a specific site in a steroid molecule was found to enhance beneficial pharmacological effects New analytical techniques evolved (e.g., GC and NMR). There are eight reactions important for preparation of monofluoroaliphatic compounds. Halogen addition to alkenes and alkynes Fluoroalkylamine reagent for replacement of a hydoxy group. Nitrosyl fluoride addition to an activated double bond Hypofluorites for electrophilic fluorination. Inorganic and heteroatom fluorides for replacement of halogen, hydroxyl, or ester groups Hydrogen fluoride for addition Perchloryl fluoride for hydrogen replacement Condensation of a monolfluorinated organic compound.

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ChemInform Abstract: STEROID‐UMLAGERUNGEN, RK. EINES 16ALPHA,17ALPHA‐EPOXY‐PREGNAN‐20‐ONS MIT FLUORWASSERSTOFF UND DIE THERMISCHE DEHYDROFLUORIERUNG

Hoff¹

1970

Chemischer Informationsdienst. Organische Chemie

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Steroid rearrangements. Reactions of a 16,17.alpha.-epoxypregnan-20-one with hydrogen fluoride. Thermal dehydrofluorinations

Abstract: p-Nitrobenzoylation of 7.-Treatment of 7 (0.15 g) with pnitrobenzoyl chloride (0.25 g) in dry pyridine (2 ml) at room temperature for 40 hr and work-up gave 0.2 g (68%) of the p-

Cited by 8 publications

References 3 publications

Bismuth(III) triflate-catalyzed rearrangement of 16α,17α-epoxy-20-oxosteroids. Synthesis and structural elucidation of new 16α-substituted 17α-alkyl-17β-methyl-Δ13-18-norsteroids

Bismuth(III) triflate-catalyzed rearrangement of 16α,17α-epoxy-20-oxosteroids. Synthesis and structural elucidation of new 16α-substituted 17α-alkyl-17β-methyl-Δ13-18-norsteroids

Modern Methods to Prepare Monofluoroaliphatic Compounds

ChemInform Abstract: STEROID‐UMLAGERUNGEN, RK. EINES 16ALPHA,17ALPHA‐EPOXY‐PREGNAN‐20‐ONS MIT FLUORWASSERSTOFF UND DIE THERMISCHE DEHYDROFLUORIERUNG

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