1-Substituted 2-heteroadamantanes

The bicyclic dioximes 4–6 and dimethoximes 7–9, which contain the functional groups in opposite positions of bridged eight‐membered rings, were synthesized. Their conformational properties and transannular interactions were investigated by spectroscopic (PE, 13C NMR) and theoretical (MMX, AM1, ab initio HF, and B3LYP) methods. While in the 3,7‐disubstituted bicyclo[3.3.1]nonane derivatives 5 and 8 the eight‐membered ring has a CC conformation favourable for through‐space interactions of the π(CN) orbitals, in the bicyclo[3.3.0]octane derivatives 4 and 7 as well as the 2,6‐disubstituted bicyclo[3.3.1]nonanes 6 and 9 the functional groups are in geometric orientations that are unfavourable for such interactions. Through‐space orbital interactions in the molecules with favourable conformations lead to a splitting of the π(CN) MOs of 0.4–0.6 eV.

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“…241°C (ref. [29] the latter methods were generally in better accordance with 240Ϫ243°C troscopy. The spectra of the difunctional compounds com-…”

Section: C-nmr Spectramentioning

confidence: 75%

Spectroscopic and Theoretical Investigations of Bicyclic Dioximes and Dimethoximes with Eight-Membered Rings

Strenge

Rademacher

1999

Eur. J. Org. Chem.

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“…Secondary amines 2a and 2b were obtained in high yields following a known general procedure that involves reductive amination of diketone 1 . 8 Thus, reaction of 1 with benzylamine followed by reduction with LiAlH 4 led to amine 2a in 58% yield. Similarly, reductive amination of 1 with phenethylamine furnished amine 2b in 51% yield.…”

Section: Resultsmentioning

confidence: 97%

Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines

Duque

Camps

Profire

et al. 2009

Bioorganic & Medicinal Chemistry

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“…The organic layers were dried (Na2S0,), and the solvents were evaporated under reduced pressure. The aldehyde (5.02 g, 96.5%) was used without further purification: NMR 6 To a solution of 3.2 g (0.017 mol) of p-toluenesulfonyl hydrazide in 20 mL of glacial acetic acid at 80 "C was added 5.02 g of the above aldehyde (0.017 mol). After 15 min at 80 "C the solution was cooled, and white crystalline solid appeared.…”

Section: Methodsmentioning

confidence: 99%

Thermal and photochemical reactions of sodium salts of .beta.-phosphono tosylhydrazones

ULMAN¹,

Sprecher²

1979

J. Org. Chem.

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Thermal and photochemical reactions of sodium salts of P-phosphono tosylhydrazones have been investigated. When the sodium salt of dimethyl a-acetylmethylphosphonate tosylhydrazone is heated, the dimethoxyphosphonyl anior , though a relatively strong base, was eliminated. On the other hand, ultraviolet irradiation of the sodium salts of P-phosphono tosylhydrazones leads to dimethoxyphosphonyl-substituted olefins, presumably via the carbene intermediate. Some of the products result from a previously unreported phosphonyl group migration to a carbene.

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1-Substituted 2-heteroadamantanes

Cited by 32 publications

References 4 publications

Spectroscopic and Theoretical Investigations of Bicyclic Dioximes and Dimethoximes with Eight-Membered Rings

Spectroscopic and Theoretical Investigations of Bicyclic Dioximes and Dimethoximes with Eight-Membered Rings

Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines

Thermal and photochemical reactions of sodium salts of .beta.-phosphono tosylhydrazones

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