Acenaphth acenaphthylene

The coupling of 1,8-diiodonaphthalene (25) with acenaphthylene (26) affords acenaphth[l,2-a]acenaphthylene (27). It should be noted that the reaction involves unusual trans elimination of H—Pd—1[32], This tetrasubstituted double bond in 11 reacts further with iodobenzene to give the [4, 3, 3]propellane 28 in 72%. This unusual reaction may be accelerated by strain activation, although it took 14 days[33]. 

From the reaction of iodobenzenes with acenaphth[l,2-a]acenaphthylene are formed propellane type products (Eq. 48) [101, 102]. The reaction with diarylacetylenes affords 9,10-diarylphenanthrenes (Eq. 49) [103,104]. 

Figure 10.7 READS-TCT calculation three-dimensional spin densities for acenaphthylene and biphenylene with one electron added. Eighty percent of the spin resides on acenaphth-alene, indicating that the Ea of acenaphthylene is greater than that of biphenylene.

Recently, an elegant synthesis of 86 was developed by Dyker et al. [86,87] (Scheme 17). Pd°-catalyzed coupling of acenaphthylene (89) and 1,8-diiodo-naphthalene provides an efficient access to acenaphth[l,2-a]acenaphthylene 90... 

Acenaphth[1,2-a]acenaphthylene, methyl-Acenaphtho[1,2-b]pyridine 7-azafluoranthene ... 

Similar acenaphth-(9,10)-acenaphthylene structures were described in the literature [199]. The formation of polymers may lead to novel highly condensed... 

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