Neighbouring Group Participation

Capon, Brian

doi:10.1007/978-1-4899-3013-2_11

Cited by 5 publications

(2 citation statements)

References 128 publications

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“…for 24 h. It was then diluted with water and the precipitate filtered off and recrystallized from ethanol. t 3,5(10) -trien (lc, 3c, 4c, 7c). -General Method: Compound la, 3a, 4a, 7a (3.16 g, 0.01 mol) was dissolved in dichloromethane (30 ml) and 3,4-dihydropyran (3 ml), and a catalytic amount of EtzO-BF3 were added.…”

Section: Methodsmentioning

confidence: 99%

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Steroids, XLI. Neighbouring Group Participation, X. Neighbouring Group Participation and Fragmentation During the Solvolysis of the Epimers of 3‐Methoxy‐16‐(tolylsulfonyloxymethyl)‐estra‐1,3,5(10)‐trien‐17‐ol

Schneider¹,

Hackler²,

Wölfling³

et al. 1989

Liebigs Ann. Chem.

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The four possible isomers of 16‐hydroxymethyl‐3‐methoxyestra‐1,3,5(10)‐trien‐17‐ol were converted into the 16‐tolylsulfonyloxymethyl‐17‐acetoxy esters 1b, 3b, 4b, 7b and into the 16‐tolylsulfonyloxymethyl‐17‐tetrahydropyranyl acetals 1c, 3c, 4c, 7c. On alkaline methanolysis of 1b and 7b, the α and β oxetanes 2 and 8 condensed to the D ring in the sterane skeleton were formed, while 3b and 4b yielded the fragmented product 5. Under similar experimental conditions, the acetals 1c, 3c, 4c, 7c were transformed into the 16‐methoxymethyl derivatives 1d, 3d, 4d, 7d.

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Section: Methodsmentioning

confidence: 99%

“…The lines of the pyrane ring in 7 c are: C-2': 98.2. C-3': 30.4,[2][3][4][5][6]0. a.d' Reversed assignments may also be possible.b.c) Two overlapping lines.…”

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confidence: 99%