Abstract
Two efficient syntheses of dibenzocyclooctadienediyne 1 were developed employing known reactions,
which utilize commercially available reagents. Both methods are
an improvement on known syntheses resulting in 41% and
43% overall yields. The latter method also offers an efficient
synthesis of dibenzocyclooctatetraene 9 ,
which is one of the key reagents now commercially unavailable.
Key words
dibenzocyclooctadienediyne - elimination - lithium - sonication
References
1 Destro R.
Pilati T.
Simonetta M.
J.
Am. Chem. Soc.
1975,
97:
658
2a Man YM.
Mak TCW.
Wong HNC.
J.
Org. Chem.
1990,
55:
3214
2b Wong HNC.
Acc. Chem. Res.
1989,
22:
145
2c Muller M.
Iyer VS.
Kubel C.
Enkelmann V.
Mullen K.
Angew.
Chem., Int. Ed. Engl.
1997,
36:
1607
3 Brettreich M.; Bendikov, M.; Chaffins,
S.; Duong, H.; Perepichka, D. F.; Helgeson, R.; Wudl, F., in press.
4a Wawzonek S.
J. Am. Chem. Soc.
1940,
62:
745
4b Bachman GB.
Hoaglin RI.
J.
Org. Chem.
1943,
8:
300
4c Wittig G.
Angew.
Chem.
1951,
63:
15
4d Bergmann ED.
Pelchowicz Z.
J. Am.
Chem. Soc.
1953,
75:
4281
4e Cava MP.
Pohlke R.
Erickson BW.
Rose JC.
Fraenkel G.
Tetrahedron
1962,
18:
1005
4f Griffin CE.
Peters JA.
J.
Org. Chem.
1963,
28:
1715
4g Vogel E.
Frass W.
Wolpers J.
Angew.
Chem.
1963,
75:
979
4h Avram M.
Dinulescu IG.
Dinu D.
Mateensen G.
Nenitzesen CD.
Tetrahedron
1963,
19:
309
4i Wong HNC.
Garratt PJ.
Sondheimer F.
J. Am. Chem. Soc.
1974,
96:
5604
4j Chan TL.
Huang NZ.
Sondheimer F.
Tetrahedron
1983,
39:
427
4k Dürr H.
Klank G.
Peters K.
von
Schnering HG.
Angew. Chem.
1983,
95:
321
4l Barton JW.
Lee DV.
Shepherd MK.
J. Chem. Soc., Perkin Trans. 1
1985,
1407
5 Fieser LF.
Pechet MM.
J. Am. Chem. Soc.
1946,
68:
2577
6a Jung ME.
Mossman AB.
Lyster MA.
J.
Org. Chem.
1978,
43:
3698
6b Kagan J.
Chen SY.
Agdeppa DA.
Watson WH.
Zabel V.
Tetrahedron Lett.
1977,
4469
7 Jung ME.
Miller SJ.
J. Am. Chem. Soc.
1981,
103:
1984
8a Hashimoto N.
Aoyama T.
Shioiri T.
Tetrahedron Lett.
1980,
21:
4619
8b Boehshar M.
Heydt H.
Regitz M.
Tetrahedron
1986,
42:
1815
9 Jigajinni VB.
Wightman RH.
Tetrahedron Lett.
1982,
23:
117
10 Chan TL.
Mak TCW.
Poon CD.
Wong HNC.
Jia JH.
Wang LL.
Tetrahedron
1986,
42:
655
11 Cope AC.
Fenton SW.
J. Am. Chem. Soc.
1951,
73:
1668
12 Boudjouk P.
Sooriyakumaran R.
Han BH.
J.
Org. Chem.
1986,
51:
2818
13 Moore JA.
Mitchell TD.
Org. Prep. Proced.
Int.
1984,
16:
411
14 Jimeno ML.
Alkorta I.
Eleguro J.
Anderson JE.
Claramunt RM.
Lavandera JL.
New
J. Chem.
1998,
1079
