217-22-1Relevant academic research and scientific papers
A convenient synthesis of dibenzo[a,c]cyclooctene based on thioenol ether reduction
Lottaz, Pierre Andre,Edwards, Timothy R. G.,Mentha, Yves G.,Burger, Ulrich
, p. 639 - 642 (2007/10/02)
9,10,11,12-Tetrahydrodibenzo[a,b]cyclooctane-9,12-diol (6) is found to be reluctant to double bond forming elimination. It gives a bridge ether (7) instead. The corresponding diketone (5) reacts with benzyl mercaptan to provide the bis-thioenol ether (8-a
The Photochemical Synthesis and Denitrogenation of 8,9-Diazodibenzoisobullvalene
Burger, Ulrich,Mentha, Yves G.,Millasson, Patricia,Lottaz, Pierre-Andre,Mareda, Jiri
, p. 1722 - 1728 (2007/10/02)
Starting from dibenzocyclooctene (4) and 4-methyl-3H-1,2,4-triazol-3,5(4H)-dione (MTAD), the strained skeleton of the title azo compound 1 is assembled in a tandem photo-Diels-Alder addition/di-?-methane rearrangement sequence.The synthesis is completed by a stepwise hydrolytic oxydation of the ensuing triazolidinedione 2 with nickel peroxide.Thermolysis of 1 in benzene solution is shown to be governed by an initial 1,3-dipolar cycloreversion which leads, via an intermediate diazo compound 11, to cyclobutaphenanthrene 8 and two further carbene-derived C16H12 products.Photolysis of 1 at 350 nm leads in modest yield (12percent), via a diazenyl diradical, to an unstable bridged bicyclobutane 10 (dibenzooctavalene).MNDO calculations suggest the latter to have a rapidly inverting, twisted structure of C2 symmetry.
BARRIERS TO RING INVERSION IN DIBENZOCYCLOOCTENE AND ITS DIHYDRO AND TETRAHYDRO DERIVATIVES BY RACEMIZATION AND NMR BANDSHAPE STUDIES
Rashidi-Ranjbar, Parviz,Sandstroem, Jan
, p. 1537 - 1540 (2007/10/02)
Dibenzocyclooctene and its 9,10-dihydro and 9,10,11,12-tetrahydro derivatives have been resolved by chromatography and their inversion barriers determined by thermal racemization.The 9,12-dihydro derivative has been studied by 1H NMR bandshape technique.
5,6-Didehydro-7-bromodibenzocyclooctene and 5,6-Didehydro-8-tert-butoxydibenzocyclooctene as Reactive Intermediates. A Convenient Synthesis of Dibenzocyclooctene
Wong, Henry Nai Ching,Sondheimer, Franz
, p. 2438 - 2440 (2007/10/02)
A convenient synthesis of dibenzocyclooctene (8) is described, which on bromination yielded 5,6,7,8-tetrabromo-5,6,7,8-tetrahydrodibenzocyclooctene (3).Dehydrobromination of 3 led to 6,7-dibromodibenzocyclooctene (9), 5-tert-butoxy-7-bromod
