1978
DOI: 10.1021/ja00493a023
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Chemistry of (2- and 3-furyl)methylenes and (2- and 3-thienyl)methylenes

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Cited by 62 publications
(36 citation statements)
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“…This is supported by the observation that treatment of the aldehyde 20c with trimethyl phosphite without the rigorous exclusion of moisture leads to cyclisation and formation of the bisphosphonate 25. Although the ring opening of thiophen-2-yl carbenes has been reported 12 we saw no evidence for this occurring with the thiophen-2-yl carbene intermediate 4a generated by the action of trialkyl phosphite on the aroylphosphonate 1a. We have therefore ruled out a pathway analogous to that shown in Scheme 8 to explain the formation of the corresponding thiophene-based bisphosphonate 10.…”
Section: Methodscontrasting
confidence: 66%
“…This is supported by the observation that treatment of the aldehyde 20c with trimethyl phosphite without the rigorous exclusion of moisture leads to cyclisation and formation of the bisphosphonate 25. Although the ring opening of thiophen-2-yl carbenes has been reported 12 we saw no evidence for this occurring with the thiophen-2-yl carbene intermediate 4a generated by the action of trialkyl phosphite on the aroylphosphonate 1a. We have therefore ruled out a pathway analogous to that shown in Scheme 8 to explain the formation of the corresponding thiophene-based bisphosphonate 10.…”
Section: Methodscontrasting
confidence: 66%
“…21,22 The intermediacy of the corresponding thienyl- and furylcarbenes was inferred from the isolation of the products of insertion into the C–H bond of cyclooctane and the formal products of dimerization. Fragmentation of the ring, to afford ring-opened products, was also observed.…”
Section: Introductionmentioning
confidence: 99%
“…This assignment was confirmed by calculations at the B3LYP/6−31G(d) level of theory, which nicely reproduced the experimental spectrum (Table 1, Figure 1). The calculations also revealed that 2c had been formed in its ( Z ) configuration, in conformity with ( Z )‐ 2a , which is the primary photoproduct of the photolysis of 3a 13. However, while UV irradiation of ( Z )‐ 2a rapidly led to ( E )/( Z ) isomerization, ( Z )‐ 2c was remarkably stable, even towards prolonged UV irradiation.…”
Section: Resultsmentioning
confidence: 92%