8-Oxa-1-aza-7-phenylbicyclo[5.2.1]decane-9,10-dione

Kubicki, Maciej; Codding, Penelope W.

doi:10.1107/s160053680100558x

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“…The X-ray structure of oxazolinedione 331b indicated that the endocyclic amide bond is more distorted than the exocyclic bond (i.e., the endocyclic N–C(O) bond is 0.038 Å longer and the endocyclic CO bond 0.014 Å shorter than the corresponding NC(O) and CO exocyclic bonds). Later, the X-ray structure of bridged oxazolidinedione 331c was reported by Kubicki ( 331c : endocyclic NC(O) = 1.368 Å; CO = 1.211 Å; exocyclic NC(O) = 1.383 Å; CO = 1.193 Å) …”

Section: Synthesis Of Bridged Lactams With Complex Ring Systems and R...mentioning

confidence: 95%

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Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Synthesis Of Bridged Lactams With Complex Ring Systems and R...mentioning

confidence: 95%

“…Later, the X-ray structure of bridged oxazolidinedione 331c was reported by Kubicki ( 331c : endocyclic N–C(O) = 1.368 Å; C=O = 1.211 Å; exocyclic N–C(O) = 1.383 Å; C=O = 1.193 Å). 392 …”

Section: Synthesis Of Bridged Lactams With Complex Ring Systems Anmentioning

confidence: 99%