Heteroatoms conjugated

A.P. Monkman, L.-O. Palsson, R.W.T. Higgins, C. Wang, M.R. Bryce, A.S. Batsanov, and J.A.K. Howard, Protonation and subsequent intramolecular hydrogen bonding as a method to control chain structure and tune luminescence in heteroatomic conjugated polymers, J. Am. Chem. Soc., 124 6049-6055, 2002. 

Both categories of sp-hybridized neutral carbon ligands, namely the all-carbon-substituted and heteroatom-conjugated allenylidene and cumulenylidene ligands, are presented in great detail by V. Cadiemo and S. E. Garcia-Garrido in the sixth and seventh chapters of this volume, respectively. 

Heteroatom-Conjugated Allenylidene and Related Cumulenylidene Ligands... 

Nucleophilic additions of alcohols, amines, thiols, and selenols to Group 8 buta-trienylidene intermediates [M]=C=C=C=CR2 have also been used in the preparation of stable heteroatom-conjugated allenylidene complexes. Thus, activation of trimethylsilyl-l,3-butadiyne HC=C-C=CSiMe3 by the iron(II) complex [FeClCp (dppe)], in methanol and in the presence of NaBPh4, resulted in the high-yield formation of the methoxy-allenylidene [FeCp =C=C=C(OMe)Me ... 

Electrophilic Attack at Other Ring Atoms, or at Heteroatoms Conjugated with the Nitrogen 512... 

The Electronic Structure of Some Heteroatom Conjugated Compounds A. J. Owen, Tetrahedron, 1961,14, 237-245. 

A. J. Owen, The electronic structure of some heteroatom conjugated compounds. Tetrahedron 14, 237 (1961). 

Now consider a heteroatomic conjugated system, e g. R2C=CH-CH=0. Draw the product that results from the heterolytic cleavage of the carbonyl bond. 

---