343925-81-5

Basic information

• Product Name: ethylidenemethylenecyclopropane
• Synonyms: ethylidenemethylenecyclopropane
• CAS NO: 343925-81-5
• Molecular Weight: 80.1295
• Mol File: 343925-81-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethylidenemethylenecyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: ethylidenemethylenecyclopropane(343925-81-5)
• EPA Substance Registry System: ethylidenemethylenecyclopropane(343925-81-5)

Safety Data

• Hazardous Substances Data: 343925-81-5(Hazardous Substances Data)

Upstream product

• 81198-98-3 cyclopropylidene-11 methyl-12 ethano-9,10 dihydro-9,10 anthracene 

Relevant articles and documents

Reactions retrodieniques. XII. Cycloreversions et rearrangements d'ethano-9,10 dihydro-9-10 anthracenes cyclopropaniques

Five Diels-Alder adducts of anthracene, containing respectively the spiro cyclopropane (3), vinylcyclopropane (4), allenylcyclopropane (5) and methylenecyclopropane systems (6 and 7) have been synthesized and their flash thermolytic behaviour investigated.Whereas the adduct 3 undergoes exclusively a retro-Diels-Alder cleavage leading to methylenecyclopropane, two types of rearrangements are observed, owing to their structure, as predominant reaction paths with compound 4-7 : the adducts 4 and 5, possessing a vinylcyclopropane unit, almost only rearrange into the corresponding cyclopentene 14 and methylenecyclopentene 15, respectively; on the other hand, the methylenecyclopropene adducts 6 and 7 undergo a more unexpected rearrangement of the anthracenic framework leading to the polycyclic methylenecyclobutanes 19 and 20.The structure proposed for 19 follows unambiguously from its spectral properties and is confirmed by its ozonolysis yielding the cyclobutanone 21.In the same way, the retro-Diels-Alder cleavage of the adducts 4-7, also observed as a minor reaction path (10-40percent), is followed by the isomerization of the firstly obtained cyclopropanic cumulenes, leading to 1,4-hexadiyne (from 5), dimethylenecyclopropane (from 6), or 1-hexen-4-yne and ethylidenemethylenecyclopropane (from 7).