1,4-Diphenylbuta-1,3-diene

Nitrosyl cyanide, generated from nitrosyl chloride and silver cyanide in chloroform at — 20 °C, affords unstable products with various dienes, e.g. butadiene and 2,3-di-methyl-1,3-butadiene. With methyl sorbate, compound 182 is produced (equation 103), thebaine (183) gives 184 (equation 104)97 and 9,10-dimethylanthracene yields the stable cycloadduct 185, which decomposes into its components on heating and consequently can serve as a source of nitrosyl cyanide. Thus heating 185 with 1,4-diphenylbuta-1,3-diene gives the dihydrooxazine 186 and dimethylanthracene (equation 105)98. 

Diphenylbuta-1,3-diene (Section Expt 6.141) is prepared by a variant of the general method in which cinnamaldehyde is similarly condensed with phenyl-acetic acid. 

Vinyl sulfoxides are useful Diels-Alder dienophiles. Thermolysis of the adducts gives rise to alkenes via sulfoxide elimination and so over the two steps the vinyl sulfoxides are the synthetic equivalents of alkynes, e.g. phenyl vinyl sulfoxide reacts with anthracene and 1,4-diphenylbuta-1,3-diene with concomitant sulfoxide elimination under the Diels-Alder conditions to give adducts (70) and (71 Scheme 15). 3-Phenylsulfinyl-a,3-unsaturated-carbonyl compounds have also been used as Diels-Alder dienophiles in chemistry developed for a synthesis of disodium prephenate and epiprephenate. With the electron rich diene (72), vinyl sulfoxides (73) and (75) gave rise to products (74 equation 33) and (76 equation 34) after hydrolysis. For the prephenate synthesis the phenylsulfinylmethylenelactone (77) was used, giving cyclohexadienone (78 Scheme 16) after sulfoxide elimination and hydrolysis. ... 

Bennett and Birge have determined a two-photon excitation spectrum of d -trans 1,4-diphenylbuta-1,3-diene in EPA glass at 77 K. The system origin of the lowest A nn state is observed at 27 900 20 cm , 130cm " below the system origin of the strongly allowed state. The short intrinsic lifetime of... 

In a later study, Barson et al had found that the acetylenic compounds (PhOCH, PhOCPh and PhOCCsCPh) are significantly less effective in reacting with benzoyloxy radicals than their corresponding olefins (styrene, stilbene and 1,4-diphenylbuta-1,3-diene respectively). 

Tellurium-containing products were not obtained when tellurium tetrachloride reacted with ethylene. The instability of this addition product makes it a desirable intermediate in the catalytic oxidation of ethylene. Patents for such a process using a solution of tellurium dioxide in hydrobromic/glacial acetic acid were issued - Diisobutylene, 1,4-diphenylbuta-diene, 2,3-diphenylbutadiene, 2,4-hexadiene , allyl bromide, allyl chloride, allyl acetate, and styrene either reduced tellurium tetrachloride to tellurium, produced compounds of indefinite composition, or did not react at all. 

In the case of the chromium carbonyl compounds the intermediacy of norbomadiene-Cr(CO) 4 has been demonstrated. 1,4-diphenylbuta-diene-Fe(CO) 3 and [(C0H5)3P]2Ni(CO)s have been recovered to >90% showing their catalytic function. UV irradiation of norbomadiene in the presence of Ni(CO)4 gives the following product resulting from a formal (2 + 2 + 2) cycloaddition reaction 571> ... 

Similarly, conjugated dienes, enynes, and diynes such as ( , )-l,4-diphenylbuta-l,3-diene 162, fE)-l,4-diphenyl-but-l-en-3-yne 163, or l,4-diphenylbuta-l,3-diyne 164 on treatment with trithiazyl trichloride (2 equiv) afforded the bisthiadiazole 165 in moderate to good yield (40-60%), depending on the reaction conditions (Scheme 24) <1997CC1493, 1997J(P 1)3189, 1998CC1207>. 

The reaction of 1,4-diphenylbuta-l,3-diene (2) with trithiazyl trichloride (3) yields a bi(thiadiazole) (4), an isothiazoloisothiazole (5), a dithiazolothiazine (6), and two thiazin-odithiatriazepines (7) and (8) by 1,2-, 1,3-, and 1,4-cycloaddition reactions (Scheme 2). The bridged-mode (/3-tether) tandem inter-[4 -E 2]/intra-[3 -E 2] cycloaddition of (ii)-2-methyl-2-nitrostyrene (9) with 1-butoxypenta-1,4-diene (10) produces stable tricyclic nitroso acetals (11) which afford, after reduction and protection, highly functionalized aminocyclopentanedimethanol triacetates (12) (Scheme 3). ... 

Bassett, J.-M., Green, M., Howard, J.A.K. and Stone, F.G.A. (1978) Formation of nona(ethyl isocyanide)diiron from penta(ethyl isocyanide)iron and reaction of penta(tert-butyl isocyanide)iron with diphenylacetylene X-ray crystal structures of nona(ethyl isocyanide)diiron and tris(tert-butyl isocyanide) l,4-bis-(tert-butylimino)-2,3-diphenylbuta-l,3-diene ... 

To our knowledge, the first example reported of a tellurium-lithium exchange reaction leading to a vinyllithium was the reaction of 2,5-diphenyltellurophene 165 with -butyllithium, giving l,4-dilithium-l,4-diphenylbuta-l,3-diene 166, which was trapped with several electrophiles leading to the corresponding disubstituted dienes 167 with retention of configuration (Scheme 95).254... 

The involvement of trimethylenemethane diradicals in deazetization of diazoalkane-allene adducts or trimethylene diradicals in the deazetization of the adducts of acyclic alkenes often leads to mixture of regioisomers and stereoisomers and from the standpoint of cyclopropane syntheses, this is undesirable. Far fewer problems of this type attend deazetization of the adducts of cyclic or polycyclic alkenes and, furthermore, even a modest amount of strain in the system activates the alkene to diazoalkane addition so that there is no need for activating substituents on the double bond. Cyclopropene is highly reactive towards diazoalkanes (see also Section 1.1.5.1.5.3.1.) and cycloaddition reactions of this type provide a ready entry into the bi-cyclo[1.1.0]butane series. The addition of diphenyldiazomethane to cyclopropene gave 4,4-diphenyl-2,3-diazabicyclo[3.1.0]hex-2-ene (1), which on photolysis gave a mixture of 2,2-diphenylbicyclo[1.1.0]butane (2) and 1,1-diphenylbuta-l,3-diene (3). ... 

In contrast, l-chloro-1-fiuorobenzocyclopropene (5a) was synthesized by the general scheme from l,2,3-trichloro-3-fluorocyclopropene and buta-f, 3-diene it is extremely sensitive towards moisture.( , )-l,4-Diphenylbuta-l,3-diene underwent addition to 1,2-dichloro-... 

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