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- W1983702748 abstract "A copper-mediated procedure for terminal alkynyl-propargyl coupling has been applied to “skipped” bis-terminal undecatetrayne and 1,4-bis(pseudo)halobut-2-ynes with the aim of preparing ring carbomers of representative strained and loose cycloalkanes, namely [N]pericyclynes. Two unprecedented, cyclic, “skipped” polyynes with CH2 vertices have been isolated as mixtures of diastereoisomers: an isomer 1 b and a dimer 2 a of [5]pericyclyne 1 a. The isomer 1 b is a cyclotetrayne with an exocyclic allene function resulting from a unique formal S process. Its structure has been established by 1H/13C HMQC and HMBC two-dimensional NMR analysis. According to density functional theory calculations, it is about 6 kcal mol−1 more stable than [5]pericyclyne (1 a). Compound 1 b can also be regarded as a C13-relaxed [4]pericyclyne, a long sought “skipped” C12 tetrayne. The dimer 2 a is a C30 ring that results from a formal SN process. It is a stable ring carbomer of cyclodecane, that is, a [10]pericyclyne, with four CH2 vertices." @default.
- W1983702748 created "2016-06-24" @default.
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- W1983702748 date "2001-03-16" @default.
- W1983702748 modified "2023-09-23" @default.
- W1983702748 title "On Ring Carbomers of Cyclobutane, Cyclopentane, and Cyclodecane and Cyclization Reactions through Bis(alkynyl-propargyl) Coupling" @default.
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- W1983702748 doi "https://doi.org/10.1002/1521-3765(20010316)7:6<1165::aid-chem1165>3.0.co;2-3" @default.
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