105542-98-1Relevant articles and documents
Scalable synthesis of 1-bicyclo[1.1.1]pentylamine via a hydrohydrazination reaction
Bunker, Kevin D.,Sach, Neal W.,Huang, Qinhua,Richardson, Paul F.
, p. 4746 - 4748 (2011)
The reaction of [1.1.1]propellane with di-tert-butyl azodicarboxylate and phenylsilane in the presence of Mn(dpm)3 to give di-tert-butyl 1-(bicyclo[1.1.1]pentan-1-yl)hydrazine-1,2-dicarboxylate is described. Subsequent deprotection gives 1-bicyclo[1.1.1]pentylhydrazine followed by reduction to give 1-bicyclo[1.1.1]pentylamine. The reported route marks a significant improvement over the previous syntheses of 1-bicyclo[1.1.1] pentylamine in terms of scalability, yield, safety, and cost.
Cubane, Bicyclo[1.1.1]pentane and Bicyclo[2.2.2]octane: Impact and Thermal Sensitiveness of Carboxyl-, Hydroxymethyl- and Iodo-substituents
Dallaston, Madeleine A.,Houston, Sevan D.,Williams, Craig M.
, p. 11966 - 11970 (2020)
With the burgeoning interest in cage motifs for bioactive molecule discovery, and the recent disclosure of 1,4-cubane-dicarboxylic acid impact sensitivity, more research into the safety profiles of cage scaffolds is required. Therefore, the impact sensitivity and thermal decomposition behavior of judiciously selected starting materials and synthetic intermediates of cubane, bicyclo[1.1.1]pentane (BCP), and bicyclo[2.2.2]octane (BCO) were evaluated via hammer test and sealed cell differential scanning calorimetry, respectively. Iodo-substituted systems were found to be more impact sensitive, whereas hydroxymethyl substitution led to more rapid thermodecomposition. Cubane was more likely to be impact sensitive with these substituents, followed by BCP, whereas all BCOs were unresponsive. The majority of derivatives were placed substantially above Yoshida thresholds—a computational indicator of sensitivity.
ADDITION OF HALOGENS TO PROPELLANE
Zefirov, N. S.,Surmina, L. S.,Sadovaya, N. K.,Koz'min, A. S.
, p. 2670 (1987)
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Synthesis of novel cage quaternary salts via nucleophilic substitution of 1,3-diiodobicyclo[1.1.1 ]pentane. Further evidence for a stable 3-iodo-1-bicyclo[1.1.1]pentyl cation
Adcock, James L.,Gakh, Andrei A.
, p. 4875 - 4878 (1992)
Nucleophilic substitution of 1,3-diiodobicyclo[1.1.1]pentane by tertiary amines and pyridines was investigated. The structure of cage quaternary salts obtained together with the observation of the competitive addition of pyridine in the reaction of [1.1.1]propellane with iodine indicate the existence of a relatively stable "hot intermediate" very close in its structure to a stabilized 3-iodo-1-bicyclo[1.1.1]pentyl cation.
A continuous flow synthesis of [1.1.1]propellane and bicyclo[1.1.1]pentane derivatives
Donnelly, Kian,Baumann, Marcus
supporting information, p. 2871 - 2874 (2021/03/23)
A continuous flow process to generate [1.1.1]propellane on demand is presented rendering solutions of [1.1.1]propellane that can directly be derivatised into various bicyclo[1.1.1]pentane (BCP) species. This was realised in throughputs up to 8.5 mmol h-1providing an attractive and straightforward access to gram quantities of selected BCP building blocks. Lastly, a continuous photochemical transformation of [1.1.1]propellane into valuable BCPs bearing mixed ester/acyl chloride moieties was developed.
