Synthesis and Mass Spectra of Adamantylphosphoryl Derivatives

Duddeck, H.; Hani, M.; Elgamal, Abdelbaset M.; Hanna, Atef G.

doi:10.1080/03086648608072822

Cited by 13 publications

(4 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In contrast to 1 , , 2 displays two types of tertiary carbons, apical and medial, thus making its selective functionalization by cationic activation challenging. ,, Therefore, use of protection/deprotection sequences − is necessary to obtain unequally difunctionalized diamantyl derivatives. Diamondoid phosphonic dichloride derivatives are typically obtained via Lewis acid catalysis, , but the direct monophosphorylation of diamantane in the AlCl 3 /PCl 3 /CH 2 Cl 2 system results in mixtures and low yields compared to that of adamantane. We found that employing a Brønsted acid − gives rise to higher yields and, most importantly, that it is applicable to cages larger than adamantane .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines

et al. 2016

View full text Add to dashboard Cite

Direct unequal C-H bond difunctionalization of phosphorylated diamantane was achieved in high yield from the corresponding phosphonates. Reduction of the functionalized phosphonates provides access to novel primary and secondary alkyl/aryl diamantane phosphines. The prepared primary diamantyl phosphines are quite air stable compared to their adamantyl and especially alkyl or aryl analogues. This finding is corroborated by comparing the singly occupied molecular orbital energy levels of the corresponding phosphine radical cations obtained by density functional theory computations.

show abstract

Section: Resultsmentioning

confidence: 99%

“…The X-ray structure is available in the Supporting Information, page S180. (9-Hydroxydiamant-4-yl)diphenylphosphine Oxide (44). (9-Hydroxydiamant-4-yl) phosphonic dichloride (14) (0.161 g, 0.5 mmol) and 4.5 mL of freshly distilled dry THF were placed under argon in a 50 mL two-neck flask.…”

Section: ■ Introductionmentioning

confidence: 99%

Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines

et al. 2016

View full text Add to dashboard Cite

show abstract

“…61 The primary phosphine 1-16 is an oily product obtained in 75% yield from the reaction of dichlorophosphine 1-15 with LiAlH 4 . 62 4-Diamantylphosphonic acid dichloride (2-28) and di-4-diamantylphosphinic acid chloride (2-29) are prepared from 2 in 22% and 59% yield respectively, 63 and 2-29 can be further with HSiCl 3 to its corresponding secondary phosphine (84%), which is highly oxygen-sensitive. The triamantylphosphine analogues of the latter have been also synthesized.…”

Section: Phosphorylation and Phosphinationmentioning

confidence: 99%

Diamondoids: functionalization and subsequent applications of perfectly defined molecular cage hydrocarbons

et al. 2014

View full text Add to dashboard Cite

The term ''diamondoid'' describes cage hydrocarbon molecules that are superimposable on the diamond lattice. Diamondoids that are formally built by face-fusing of adamantane units, namely diamantane, triamantane, tetramantane, etc., have fascinated chemists since the beginning of the last century. The functionalization of these perfectly defined (C,H)-molecules is described here. Thus, diamondoid halides and diamondoid alcohols are first rank precursors for amino and phosphine-substituted diamondoids that have proved to be highly useful in therapeutic applications and metal catalysis, respectively. The extent of functionalization and polyfunctionalization achieved for adamantane and diamantane, and the synthesis and applications of the resulting organohybrids are illustrated, revealing their high potential in fields such as organocatalysis, polymers, molecular electronics and mechanics.

show abstract

“…Instead of phosphorus trichloride other Pnucleophiles can be used: phosphorus tribromide leads (after hydrolysis) to alkylphosphonic dibro mides [3], dichlorophosphines to diorganophosphinic chlorides [4 -7]. Aluminium trichloride was successfully substituted by aluminium tribromide [8 ], and also by anhydrous sulfuric acid [4 -6 , 9, 10].…”

Section: Introductionmentioning

confidence: 99%