75155-50-9Relevant academic research and scientific papers
o-Quinonid Compounds. Part 18. Stabilised 2,3-Naphthoquinodimethanes via Transient 1,3-Diphenylbenzinden-2-one
Jones, David W.,Pomfret, Alan,Wife, Richard L.
, p. 459 - 466 (2007/10/02)
1,3-Diphenylbenzinden-2-one (8) can be reversibly generated by thermolysis of its formal (?4s + ?4s)-dimer (11) which is itself available in 5 steps from benzindan-1,3-dione; (8) adds stereospecifically to cis- and trans-but-2-ene.Photodecarbonylation of the adducts (23), (21), and (22) derived by trapping (8) with norbornadiene, trimethylmaleimide, and the dienophile (24) gives the sterically stabilized 2,3-napththoquinodimethanes (29), (25), and (26) respectively.These are long-lived in fluid solution at 20 deg C and were characterised by u.v.-visible spectroscopy and as their adducts with 4-phenyltriazoline-3,5-dione (PTD). 1,3,4,9-Tetraphenylbenzinden-2-one (37) generated by reaction of its dibromide (10; X = O, Y = Br) with sodium iodide forms the formal (?6s + Π6s)-dimer (35).Dissociation of (35) in the presence of N-phenylmaleimide gives the adduct (15).
Stabilised 2,3-Naphthoquinodimethanes via Transient 1,3-Diphenylbenzinden-2-one
Jones, David W.,Pomfret, Alan,Wife, Richard L.
, p. 463 - 464 (2007/10/02)
1,3-Diphenylbenzinden-2-one (5) reversibly generated by thermal dissociation of its (?4 + ?4)-dimer (4) adds stereospecifically to cis- and trans-but-2-ene; the related adducts (6) and (7) undergo smooth photodecarbonylation to the long-lived 2,3-naphthoquinodimethanes (2; R1 = R2 = Me) and (2; R1,R2 = 4).
