HOMOALLYL AND HOMOBENZYL ALCOHOLS BY THE HYDROBORATION METHOD<sup>1</sup>

Winstein, S.; Allred, Evan L.; Sonnenberg, Joseph

doi:10.1021/ja01530a072

Cited by 9 publications

(2 citation statements)

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“…Samples of this ketone collected by gas-liquid partition chromatography at 130°( 10% DC-710 on Chromosorb P) had the same retention time (4.8 min) and the same infrared spectrum as an authentic sample prepared by the method of Wanzlick, et al 3 The carbonyl absorption was at 1755 cm-1 (lit.11 1755 cm-1).…”

Section: Methodsmentioning

confidence: 99%

Addition of nitrosyl chloride to olefins. Synthesis of some chloro ketones

Ponder¹,

Walker²

1967

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Addition of nitrosyl chloride to olefins. Synthesis of some chloro ketones

Ponder¹,

Walker²

1967

J. Org. Chem.

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“…The low purity of the crude product necessitated purification by conversion to the t-Boc derivative followed by TFA hydrolysis-decarboxylation (35% over 3 steps). Alkylation of the lithium enolate of methyl isobutyrate with homoallylic cyclopentenyl tosylate 17 28 in THF and subsequent hydrolysis of the resulting methyl ester intermediate gave α-cyclopentenyl isobutyric acid 18 in high overall yield. Curtius rearrangement with diphenylphosphoryl azide,29 conversion of the resulting isocyanate to the carbamate 19 (An = p -anisyl) with p -methoxybenzyl alcohol, and alkaline hydrolysis afforded geminal dimethyl analogue 20 .…”

Section: Synthesis Of Cyclopentenylmethylaminesmentioning

confidence: 99%

Scope and Mechanism of Intramolecular Aziridination of Cyclopent-3-enyl-methylamines to 1-Azatricyclo[2.2.1.0^2,6]heptanes with Lead Tetraacetate

Faraldos

Coates

2009

J. Am. Chem. Soc.

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A series of seven cyclopent-3-en-1-ylmethylamines bearing one, two, or three methyl substituents at the C2, C3, C4, or C α positions, including the unsubstituted parent, was accessed by ring-closing metatheses of α,α-diallylacetonitrile (or methallyl variants) and α,α-diallylacetone followed by hydride reductions, or by Curtius degradations of α,α-dimethyl-and 2,2,3-trimethylcyclopent-3-enylacetic acids. Oxidation of the primary amines with Pb(OAc) 4 in CH 2 Cl 2 , CHCl 3 or benzene in the presence of K 2 CO 3 effected efficient intramolecular aziridinations, in all cases except the α-methyl analogue (16), to form the corresponding 1-azatricyclo[2.2.1.0 2,6 ]heptanes, including the novel monoterpene analogues, 1-azatricyclene and the 2-azatricyclene enantiomers. The cumulative rate increases of aziridination reactions observed by 1 H NMR spectroscopy in CDCl 3 resulting from the presence of one or two methyl groups on the cyclopentene double bond, in comparison to the rate of the unsubstituted parent amine (1 : 17.5 : >280), indicate a highly electrophilic intermediate as the nitrene donor and a symmetrical aziridine-like transition state. A mechanism is outlined in which the amine displaces an acetate ligand from Pb(OAc) 4 to form a lead(IV) amide intermediate RNHPb(OAc) 3 proposed as the actual aziridinating species.

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Hydration of Olefins, Dienes, and Acetylenes via Hydroboration

Zweifel

Brown

2011

Organic Reactions

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The hydroboration of olefins, dienes, and acetylenes involves the addition of a boron‐hydrogen bond to the carbon‐carbon multiple bond. This reaction provides a new, convenient route to the corresponding organoboranes and makes them readily available as intermediates in organic synthesis. One of the important reactions that the organoboranes undero is the rapid and essentially quantitative oxidation with alkaline hydrogen peroxide. The hydroboration of olefins involves a cis addition of the boron hydrogen bond, the boron atom becoming attached to the less substituted of the two olefinic carbon atoms of the double bond. This chapter surveys the available information on the hydration of olefins, dienes, acetylenes, and their derivatives by the hydroboration‐oxidation procedure.

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HOMOALLYL AND HOMOBENZYL ALCOHOLS BY THE HYDROBORATION METHOD¹

Cited by 9 publications

References 0 publications

Addition of nitrosyl chloride to olefins. Synthesis of some chloro ketones

Addition of nitrosyl chloride to olefins. Synthesis of some chloro ketones

Scope and Mechanism of Intramolecular Aziridination of Cyclopent-3-enyl-methylamines to 1-Azatricyclo[2.2.1.0^2,6]heptanes with Lead Tetraacetate

Hydration of Olefins, Dienes, and Acetylenes via Hydroboration

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HOMOALLYL AND HOMOBENZYL ALCOHOLS BY THE HYDROBORATION METHOD1

Cited by 9 publications

References 0 publications

Addition of nitrosyl chloride to olefins. Synthesis of some chloro ketones

Addition of nitrosyl chloride to olefins. Synthesis of some chloro ketones

Scope and Mechanism of Intramolecular Aziridination of Cyclopent-3-enyl-methylamines to 1-Azatricyclo[2.2.1.02,6]heptanes with Lead Tetraacetate

Hydration of Olefins, Dienes, and Acetylenes via Hydroboration

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Product

Resources

About

HOMOALLYL AND HOMOBENZYL ALCOHOLS BY THE HYDROBORATION METHOD¹

Scope and Mechanism of Intramolecular Aziridination of Cyclopent-3-enyl-methylamines to 1-Azatricyclo[2.2.1.0^2,6]heptanes with Lead Tetraacetate