The Diels-Alder reaction of transient nitrosoguanidines: a new class of N-O heterodienophiles and a novel method for the synthesis of functionalized guanidines
Why this work is in the frame
A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.
Bibliographic record
Abstract
This thesis is a summary of research conducted since September 2001 at the University of Toronto in the laboratory of Dr. Robert A. Batey. This manuscript is divided into two chapters. In chapter one, the Diels-Alder reaction of nitrosoguanidines is discussed. This includes the intermolecular, intramolecular and diastereoselective versions of the reaction. In all cases, the reaction proceeds via oxidation of a hydroxylguanidine to generate a transient nitrosoguanidine intermediate that is subsequently trapped in situ with a 1,3-diene. The reaction proceeds in high yield and excellent regioselectivity and constitutes a new class of N-O heterodienophiles. Chapter two details the synthesis of functionalized guanidines via simple transformations of the initial cycloadducts discussed in chapter one. Simple manipulations of the cycloadducts generated via this novel methodology can generate a number of synthetically useful guanidines in high yield and few synthetic steps. Finally the synthesis of a number of “privileged” guanidine structures is discussed featuring this methodology.
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Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.003 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.002 | 0.001 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.001 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it