Bibliographic record
Abstract
(5-Chloro-1-aza-5-stannabicyclo[3.3.3]undecane) [93253-73-7] C9H18ClNSn (MW 294.41) InChI = 1S/C9H18N.ClH.Sn/c1-4-7-10(8-5-2)9-6-3;;/h1-9H2;1H;/q;;+1/p-1 InChIKey = BRPCJQRIZVVNKX-UHFFFAOYSA-M (precursor to organostannatranes that enable facile transfer of apical group due to intramolecular activation; selective alkyl transfer agent precursor) Alternate Name: 1-aza-5-chloro-5-stannabicyclo[3.3.3]undecane. Physical Data: mp 236–238 °C (EtOH),1 222–224 °C (MeOH).2 Solubility: soluble in Et2O, THF, EtOAc, CH2Cl2, and hexanes; slightly soluble in MeCN, MeOH, and i-PrOH; insoluble in H2O and aq. HCl. Form Supplied in: commercially available solid. Analysis of Reagent Purity: 13C and 119Sn NMR.3 Preparative Methods: initially prepared by transmetalation of N(CH2CH2CH2MgCl)34, 5 with SnCl4 in 12–15% yield. Subsequently, hydrozirconation of N(CH2CH–CH2)3 with Cp2ZrHCl followed by transmetalation with SnCl4 furnished 5-chloro-1-aza-5-stannabicyclo[3.3.3]undecane in 50% yield.2 Alternatively, 5-chloro-1-aza-5-stannabicyclo[3.3.3]undecane is prepared in 40% yield from N(CH2CH2CH2SnMe3)3 by thermal redistribution with Me2SnCl2.1, 5 N(CH2CH2CH2SnMe3)3 is synthesized by reacting N(CH2CH2CH2Cl)3 with Me3SnNa in liquid ammonia at −78 °C. Drawbacks to the preparation of chlorostannatrane by these routes are low yields, handling of volatile methyltin derivatives, harsh conditions, and/or expensive reagents. A scalable, two-step synthesis that remedies the former issues consists of the thermal redistribution of N(CH2CH2CH2SnBu3)3 with SnCl4 (eq 1). The tributylstannane N(CH2CH2CH2SnBu3)3 is accessible in 66% yield by the Pd/Al2O3-catalyzed hydrostannation of N(CH2CHCH2)3 with Bu3SnH, or alternatively, by the substitution of N(CH2CH2CH2Cl)3 with Bu3SnLi in 78% yield.6 (1) Purification: acid/base extraction6 or recrystallization from MeOH.2 Handling, Storage, and Precautions: toxic by ingestion and is a skin, eye, and respiratory tract irritant.7
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.008 | 0.003 |
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 itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".