Developments in cycloproparene chemistry

Advances in the Synthesis and Applications of Three Membered Sila, Sila‐Aza/‐Phospha/‐Oxa/‐Thia Cyclopropanes

“…Unlike silacyclopropanes, which have received much attention due to ring strain and unique reactivities, silacyclopropabenzene was continued as an unprecedented ring system of this class may be due to the lack of suitable synthetic methods. The traditional synthetic methods for cyclopropabenzene [ 30 ] /silacyclopropanes preparation were not suitable for the synthesis of a benzene fused silacyclopropene ring systems (silacyclopropabenzenes).…”

Interrelations in the Thermochemistry of Cyclopropanes

“…And, for the highly strained cyclopropene, the change upon formation of benzocyclopropene (20, n = 3) has been increased to some (90 ± 5) kJ mol −1 . This phenomenal increase of strain upon benzoannelation of the cyclopropene has been discussed at considerable length 106 in terms of bond fixation: these changes may be related to the relative stability of cycloalkane rings with appended endo-and exocyclic double bonds. But we lack thermochemical information about any exo-methylene or keto derivative of benzocyclopropene or of benzocyclobutene to parallel the available data for the related, but one-ring, species.…”

Studies in the Cycloproparene Series: Unexpected Products from Peterson Olefinations

“…The class of strained aromatic hydrocarbons known as the cycloproparenes, and illustrated by parent 1H-cyclopropabenzene (1) and 1H-cyclopropa[b]naphthalene (2), has provided much fascinating chemistry [1,2] since Anet and Anet [3] reported the first authenticated derivative in 1964. The fact [4,5] that the pK a of 1 is ca.…”