Di‐ <i>Tert</i> ‐Butyl Hyponitrite
Bibliographic record
Abstract
[14976-54-6] C8H18N2O2 (MW 174.24) InChI = 1S/C8H18N2O2/c1-7(2,3)11-9-10-12-8(4,5)6/h1-6H3 InChIKey = OAPFBXRHYINFDV-UHFFFAOYSA-N (E) [82554-97-0] C8H18N2O2 InChI = 1S/C8H18N2O2/c1-7(2,3)11-9-10-12-8(4,5)6/h1-6H3/b10-9+ InChIKey = OAPFBXRHYINFDV-MDZDMXLPSA-N (a convenient, low-temperature source of tert-butoxyl radicals1; induces serial cyclization of polyunsaturated hydroperoxides,2 rearrangement of allylic hydroperoxides,3 and reduction of alkyl halides or dialkyl sulfides with Et3SiH4; used in radical-trapping experiments5; and as initiator for dimerization6 and polymerization7) Alternative Names: DTBN; TBHN; DBH; BONNOB. Physical Data: white crystals mp 84.5 °C (dec)1d; volatile (0.1 mmHg at rt)1a; 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 18H)18; 13C NMR (CDCl3, 75.5 MHz) δ 81.4, 28.0.18 Solubility: insol H2O; sol common organic solvents (e.g. hexane, benzene, toluene, CCl4, and EtOH). Analysis of Reagent Purity: NMR (CDCl3, δ) 1H 1.33 (s); IR (cm−1) 2959, 1368, 1183, 9951a; for IR and Raman band assignments, see Ogle et al.8; UV (λmax, pentane) 223.4 nm (ϵ 7140 M−1 cm−1)1d; the trans structure has been established by X-ray analysis.8 Preparative Method: obtained in 80–90% yield by reaction of sodium hyponitrite with tert-BuBr in the presence of Iron(III) Chloride or Zinc Chloride.9 The preparation of sodium hyponitrite (from Na, benzophenone, and nitric oxide)10a must be performed with extreme care.10b Handling, Storage, and Precautions: although DTBN appears to be insensitive to scratching and is considered as safe,1a it can detonate when struck.1d Mixtures of DTBN with formamides undergo violent reaction or explosion when heated at 60–70 °C.6 Due to the potential risk of explosion, it is strongly recommended that all operations involving DTBN be carried out behind a safety shield using tongs, gloves, and a safety mask. Since DTBN is quite volatile, most of the unchanged material can be conveniently removed at the end of a reaction by flushing the mixture with N2 or Ar.5,11a Solid DTBN can be kept intact for several months at −10 °C or below.
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How this classification was reachedexpand
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 | 0.000 | 0.003 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.001 | 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) | 0.100 | 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 itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, 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".