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The isomer 158a can further exist either as the conformer 158a1 or 158a2 or as an equilibrium mixture of both. One obtains the conformer 158a2 on flipping the ring A in 158a1. Likewise, the two different conformers for the isomer 158b are 158b1 and 158b2. 0 kcal mol−1, respectively. Now, we can put together the operating anomeric and steric effects for each conformer and calculate the net relative energies. 4) kcal mol−1. 2 kcal mol−1. 3 kcal mol−1. 2 kcal mol−1. 4 kcal mol−1. 5 kcal mol−1. With such a large energy difference, the isomer 158a must exist as the conformer 158a1 predominantly.

62 is an example of 1,4-elimination that is followed by decarboxylation of the respective amidinium carboxylates (X = amidinium ion) to obtain the same E,Z-macrolide [30, 31]. The fragmentation was considered by Eschenmoser to take place in two consecutive steps: (a) both the ring oxygen atoms have one electron pair orbital each in an antiperiplanar orientation to stereoelectronically eject the tosylate ion via cleavage of the ring rC–C bond and generate the dipolar ions 214, and (b) the pC8–C9 bond in 215 emerges from the stereoelectronically controlled decarboxylation for having rC8–CO2- bond antiperiplanar to rC9–O bond.

We shall now turn to the internal SN2 reaction on a sp3 carbon. Purely on account of geometrical constraints imposed in achieving the collinear alignment, 2 Reactions at Saturated and Unsaturated Carbons 51 Baldwin proposed a set of rules for such ring closure reactions [4]. The reactions were designated by a numerical prefix which denotes the size of the ring to be formed, followed by the term exo or endo depending upon whether the bond breaking is exocyclic or endocyclic to the ring thus formed.

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