Solvomercuration-demercuration. IV. Monohydration of representative dienes via oxymercuration-demercuration

Brown, Herbert C.; Geoghegan, Philip J.; Lynch, Gary J.; Kurek, Joseph T.

doi:10.1021/jo00977a018

Cited by 35 publications

(14 citation statements)

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“…The same phenomenon may be involved in the hydration of (23) to form diol (8). However, the stereochemistry observed in this case would be explicable on simple steric grounds alone.…”

Section: Resultsmentioning

confidence: 72%

Syntheses and crystal structures of seven alicyclic diols which crystallise with layer structures instead of the helical tubuland inclusion lattice

Hawkins¹,

Scudder²,

Craig³

et al. 1990

J. Chem. Soc., Perkin Trans. 2

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In an exploration of the possibility of modifying the shape and size of the helical canal host structure known to occur in crystals of several bi-and tri-cyclic diols, w e report the syntheses and crystal structures of seven further diols: endo -2,endo -6 -di hydroxy -2,6 -d imet hyl bicyclo [ 3.3.1 3 nonane (5); endo-2,endo-6-dihydroxy-2,6-dimethyl-9-thiabicyclo[3.3.1]nonane (6); 2,6-dihydroxy-2,6d imet h yltricyclo [ 3.3.1 .I 397] deca ne (7) ; anti-4,anti-8 -d i h ydroxy -4,8d imet h yl -2t h iatricyclo [ 3.3.1 . 1 397]decane (9); anti-2,anti-7dihydroxy-2,7-diethyltricyclo[4.3.1 .l 3*8] undecane (I 0); and syn-2,anti-8-dihydroxy-2,8-dimethyltricyclo[5.3.1 .I 399]dodecane (1 1 ). All seven of these adopt similar layered crystal structures.The properties characteristic of these structures are: two-dimensional hydrogen bonding of diol molecules within the layers, maximised hydrogen bonding for each diol, an absence of inter-layer hydrogen bonding, and the occurrence of cycles of four hydrogen bonds connecting four diol molecules within the layers. The closed cycles of hydrogen bonds are in contrast with the extended helical spines characteristic of the helical canal host lattice. The layered diol structures do not include guests and do not involve spontaneous resolution of the diol molecules.Paper 9/03056E

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“…The same phenomenon may be involved in the hydration of (23) to form diol (8). However, the stereochemistry observed in this case would be explicable on simple steric grounds alone.…”

Section: Resultsmentioning

confidence: 72%

Syntheses and crystal structures of seven alicyclic diols which crystallise with layer structures instead of the helical tubuland inclusion lattice

Hawkins¹,

Scudder²,

Craig³

et al. 1990

J. Chem. Soc., Perkin Trans. 2

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“…Although the two trisubstituted double bonds in the diene 3a are so similar that totally regioselective hydroxylation was not expected to be feasible, reverse addition, i.e., addition of the mercury(II) acetate to the diene according to Brown et al (1972), gave the terpenols 4a and 5 in a ratio of 91:9. A fraction containing the desired terpenol, 4a, and the terpenol 5 in a ratio of 97:3 was isolated from the crude product by column chromatography.…”

Section: Resultsmentioning

confidence: 99%

“…Conventional work-up procedures and distillation of the product gave a colorless oil (16.9 g; 77.2%); bp 77°C/ 40mm Hg, containing 98.0% (GC-MS) of (E)-2,6-dimethyl-2,6-octadiene (3a) . Solid mercury(II) acetate (3.2 g; 10 mmol) was added in one batch to a stirred solution of the diene (3a) (1.38 g; 10 mmol) in THF (40 ml) and water (10 ml) at 22°C to produce a yellow reaction mixture (Brown et al, 1972).…”

Section: Reference Compoundsmentioning

confidence: 99%

“…The reaction mixture was stirred for 30 min, after which the supernatant solution was decanted from the mercury and saturated with K2CO3, resulting in the separation of the THF layer containing the organic material from the saturated K2CO3 solution. Careful concentration of the THF phase on a rotary evaporator gave a mixture of the organic products (1.41 g) containing the starting material (3a), an unidentified product that could possibly be a cyclic ether formed from the starting material (Brown et al, 1972), the two terpenols (4a) and (5), and 2,6-dimethylocta-2,6-diol (6) in a ratio of 24:33:29:3:11.…”

Section: Reference Compoundsmentioning

confidence: 99%

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Burger

Petersen

Weber

et al. 2002

Journal of Chemical Ecology

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Using gas chromatography with flame ionization detection (FID) and electroantennographic detection (EAD) in parallel, butanoic acid, skatole, and (E)-2,6-dimethyl-6-octen-2-ol were identified as constituents of the abdominal sexattracting secretion of the male dung beetle, Kheper subaeneus, which reproducibly elicited EAD responses in male and female antennae. This is the first report of the occurrence of (E)-2,6-dimethyl-6-octen-2-ol as a natural product, for which the name (E)-subaeneol is proposed. In some experiments, a few other constituents of the secretion also gave reproducible responses in specific male and female antennae but did not elicit responses when the analyses were repeated with other antennae. The major volatile constituent of the secretion, identified as (S)-(C)-2,6-dimethyl-5-heptenoic acid, is one of these EAD-active compounds. Both this compound and (E)-2,6-dimethyl-6-octen-2-ol were synthesized from authentic starting materials for comparison with the natural products.

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“…(38)]["1. Stork has utilized dichlorocarbene additions to enol acetates as a means of ring expanding cyclic ketones to enones [eq.…”

Section: Carbene Transfermentioning

confidence: 99%

Organomercury Compounds in Organic Synthesis

Larock

1985

Reactivity and Structure Concepts in Organic Chemistry

102

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Organomercurials have been known since 1850 and many synthetic routes to these compounds presently exist. The ability of these compounds to accommodate a wide variety of functional groups and to tolerate quite diverse reaction conditions makes them attractive as synthetic intermediates. While the ~~lv~mercuration-demercuration and divalent carbon transfer reactions remain the most widely used of the organomercurial reactions, a number of new synthetic procedures employing organomercurials have been developed in recent years. Many of these involve transmetallation reactions with palladium salts.

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Solvomercuration-demercuration. IV. Monohydration of representative dienes via oxymercuration-demercuration

Cited by 35 publications

References 1 publication

Syntheses and crystal structures of seven alicyclic diols which crystallise with layer structures instead of the helical tubuland inclusion lattice

Syntheses and crystal structures of seven alicyclic diols which crystallise with layer structures instead of the helical tubuland inclusion lattice

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Organomercury Compounds in Organic Synthesis

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