Heteropentalene mesomeric betaines of type C: Progress since the early 1980s

Heterocycles

Volumn 75, Issue 1, 2008, Pages 1-33

  Moderhack, Dietrich ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 43649097473     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-07-619     Document Type: Article

References (102)

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7. 1a this denomination is not recommended
8. For the first example to be prepared, see. Potts K.T., and Marshall J.C. J Org. Chem. 41 (1976) 129 [this compound (like type A,B, and D members) was then termed 'heteropentalene with ylidic characteristics:' K.T. Potts, 'The Chemistry of Heterocyclic Compounds: Heteropentalenes,' Vol. 30, ed. by A. Weissberger and E.C. Taylor, John Wiley & Sons, New York, 1977, pp. 317-379]
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87. Bird C.W. Tetrahedron 43 (1987) 4725
88. 9c,10 it is assumed that C(3a) of the type C' isomer resonates at δ 150.4.
89. 1b).
90. 18
91. Tsuge O., Kanemasa S., and Hamamoto T. Chem. Lett (1983) 763 Interestingly, the cycloadduct (83) on treatment with triethylamine looses sulfur to give the respective 3-benzylidene-3H pyrrolo[1,2-c]imidazole; this species may undergo ring closure into a tetracycle that is stabilized by dehydrogenation
92. 19
93. Tsuge O., Kanemasa S., and Hamamoto T. Chem. Lett (1983) 85 The endo isomer of 89 did not result because of steric hindrance. In addition to dimethyl maleate, dimethyl fumarate and maleoand fumaronitrile were studied; as the reactions were carried out in boiling benzene only, epithio cycloadducts were the sole products (obtained as mixtures of stereoisomers)
94. 37a (Scheme 11).
95. Tsuge O., Kanemasa S., and Hamamoto T. Heterocycles 20 (1983) 647
96. 1c
97. 61
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101. This unexpected valence isomerism was first observed with the type C' isomers of series (4). Moderhack D., and Decker D. Heterocycles 37 (1994) 683
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